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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 65| Part 11| November 2009| Page m1486
https://doi.org/10.1107/S1600536809042731

(η6-Benzo­phenone)(η5-penta­methyl­cyclo­penta­dien­yl)ruthenium(II) tetra­phenyl­borate

Bradley T. Loughrey,a Kevin Nadin,b Michael L. Williamsa and Peter C. Healya*

aEskitis Institute for Cell and Molecular Therapies, Griffith University, Brisbane 4111, Australia, and bDépartement de Chimie, Faculté des Sciences, Université d'Orléans, Orléans BP 6759 45067, France
*Correspondence e-mail: P.Healy@griffith.edu.au

(Received 13 October 2009; accepted 17 October 2009; online 31 October 2009)

The structure of the title compound, [Ru(C10H15)(C13H10O)](C24H20B), consists of discrete [Cp*Ru(II)benzophenone] cations and tetra­phenyl­borate anions (Cp* = penta­methyl­cyclo­penta­dien­yl). Tethering the Cp*Ru group to one aryl ring of benzophenone results in average values of 1.42 (1) and 1.38 (1) Å for the C—C bond lengths in the Ru-tethered and untethered phenyl rings, respectively. The dihedral angle between the benzene and phenyl rings of the benzophenone group is 50.5 (1)°.

Related literature

For background to our research into the structural and biological properties of ionic Ru(II) organometallic complex salts [Cp*Ru(II)-arene]+X−, 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., Williams, M. L., Healy, P. C., Innocenti, A., Vullo, D., Supuran, C. T., Parsons, P. G. & Poulsen, S.-A. (2009). J. Biol. Inorg. Chem. 14, 935-945.]); For related structures, see: Moncol & Coppens (2004[Moncol, J. & Coppens, P. (2004). Private communication (refcode BPHENO12). CCDC, Cambridge, England.]); Gemel et al. (1996[Gemel, C., Mereiter, K., Schmid, R. & Kirchner, K. (1996). Organometallics, 15, 532-542.]).

[Scheme 1]

Experimental

Crystal data

  • [Ru(C10H15)(C13H10O)](C24H20B)

  • Mr = 737.71

  • Monoclinic, P 21 /n

  • a = 11.6754 (8) Å

  • b = 20.5730 (12) Å

  • c = 15.6245 (9) Å

  • β = 91.250 (6)°

  • V = 3752.1 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.45 mm−1

  • T = 296 K

  • 0.30 × 0.27 × 0.13 mm
Data collection

  • Oxford-Diffraction GEMINI S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.876, Tmax = 0.943

  • 34346 measured reflections

  • 8604 independent reflections

  • 6521 reflections with I > 2σ(I)

  • Rint = 0.045
Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.110

  • S = 1.02

  • 8604 reflections

  • 451 parameters

  • H-atom parameters constrained

  • Δρmax = 1.01 e Å−3

  • Δρmin = −0.31 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809042731/lh2927sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042731/lh2927Isup2.hkl

checkCIF report


Comment top

As part of our continued investigation into the structural and biological properties of ionic Ru(II) organometallic complex salts [Cp*Ru(II)-arene]+X- (Loughrey et al., 2008, 2009), we have prepared the mono substituted adduct of Cp*Ru and benzophenone as the tetraphenylborate salt. The compound was prepared in 49% yield through the reaction of RuCl3.xH2O with an excess of benzophenone and HCp* in ethanol and isolated as the crystalline tetraphenylborate salt through addition of an aqueous solution of NaBPh4.

The compound crystallizes as discrete cations and anions (Fig. 1). No significant C-H···O interactions are observed between the phenyl and methyl protons and the ketone oxygen. The dihedral angle between the two aryl rings of the benzophenone is 50.5 (1)° and comparable to the value of 53.75 (6)° reported for the parent monoclinic benzophenone (Moncol & Coppens, 2004). The Ru-C bond lengths in the cation are also similar to those reported for other [Cp*Ru(arene)]+ complexes (Gemel et al., 1996; Loughrey et al., 2008). The average value of 1.42 (1)Å for the C-C bond lengths in the Ru tethered phenyl ring (C11-C16) is 0.04Å longer than the average value of 1.38 (1)Å observed for the free phenyl ring (C18-C23), the latter being marginally shorter than the value of 1.392 (5)Å for the parent benzophenone.

Related literature top

For background to our research into the structural and biological properties of ionic Ru(II) organometallic complex salts [Cp*Ru(II)-arene]+X-, see: Loughrey et al. (2008, 2009); For related structures, see: Moncol & Coppens (2004); Gemel et al. (1996).

Experimental top

Benzophenone (0.8 g, 4.39 mmol) and HCp* (0.3 ml, 1.88 mmol) were 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 10 h to yield a golden brown coloured solution. The solvent was concentrated in vacuo with the remaining residue being redissolved in an ether/water partition (20 ml/20 ml). The aqueous portion was retained and washed with a further three aliquots of diethyl ether (20 ml). The aqueous layer was mixed slowly with an aqueous solution of sodium tetraphenylborate (5 ml, 0.30 M). The resulting cream coloured precipitate was filtered from solution 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 crystalline precipitate was then filtered from solution and dried in vacuo. Yield = 0.273 g, 48.7%. 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 1.81 (s, 15H, C5(C5H15)), 6.07–6.11 (m, 3H, C6H5 meta and para), 6.30–6.31 (m, 2H, C6H5 ortho), 6.72–6.75 (m, 4H, B(C6H5)4 para), 6.85–6.89 (m, 8H, B(C6H5)4 meta), 7.15–7.18 (m, 8H, B(C6H5)4 ortho), 7.54–7.7.58 (m, 2H, C6H5 meta), 7.69–7.72 (m, 1H, C6H5 para), 7.79–7.82 (m, 2H, C6H5 ortho). 13C (d6DMSO), δ 9.74 (C5 (C5H15)), 87.42 (2CH, aromatic), 87.67 (2CH, aromatic), 89.03 (1CH, aromatic), 94.82 (1CH, aromatic), 97.06 (C5(C5H15)), 121.43 (4CH, B(C6H5)4), 125.22 (8CH, B(C6H5)4), 128.89 (2CH, aromatic), 129.48 (2CH, aromatic), 133.83 (1CH, aromatic), 135.48 (8CH, B(C6H5)4), 135.79 (1CH, aromatic), 162.72, 163.12, 163.51, 163.90 (4CH, B(C6H5)4), (signals split by 11B), 192.86 (C=O). ESMS (m/z) +ve ion, calcd m/z for [(η5-C5(CH3)5) Ru(η6-C6H5COC6H5)+] 418.51, found 418.85 (100%), -ve ion, calcd m/z for B(C6H5)4 319.25, found 319.05 (100%). calcd % for C47H45OBRu C 76.5, H 6.15, found C 76.2, H 6.14.

Refinement top

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 continued investigation into the structural and biological properties of ionic Ru(II) organometallic complex salts [Cp*Ru(II)-arene]+X- (Loughrey et al., 2008, 2009), we have prepared the mono substituted adduct of Cp*Ru and benzophenone as the tetraphenylborate salt. The compound was prepared in 49% yield through the reaction of RuCl3.xH2O with an excess of benzophenone and HCp* in ethanol and isolated as the crystalline tetraphenylborate salt through addition of an aqueous solution of NaBPh4.

The compound crystallizes as discrete cations and anions (Fig. 1). No significant C-H···O interactions are observed between the phenyl and methyl protons and the ketone oxygen. The dihedral angle between the two aryl rings of the benzophenone is 50.5 (1)° and comparable to the value of 53.75 (6)° reported for the parent monoclinic benzophenone (Moncol & Coppens, 2004). The Ru-C bond lengths in the cation are also similar to those reported for other [Cp*Ru(arene)]+ complexes (Gemel et al., 1996; Loughrey et al., 2008). The average value of 1.42 (1)Å for the C-C bond lengths in the Ru tethered phenyl ring (C11-C16) is 0.04Å longer than the average value of 1.38 (1)Å observed for the free phenyl ring (C18-C23), the latter being marginally shorter than the value of 1.392 (5)Å for the parent benzophenone.

For background to our research into the structural and biological properties of ionic Ru(II) organometallic complex salts [Cp*Ru(II)-arene]+X-, see: Loughrey et al. (2008, 2009); For related structures, see: Moncol & Coppens (2004); Gemel et al. (1996).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), with atom labels and 40% probability displacement ellipsoids for the non-H atoms.
(η6-Benzophenone)(η5-pentamethylcyclopentadienyl)ruthenium(II) tetraphenylborate top
Crystal data top
C23H25ORu+·C24H20B−F(000) = 1536
Mr = 737.71Dx = 1.306 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ynCell parameters from 10435 reflections
a = 11.6754 (8) Åθ = 2.8–32.8°
b = 20.5730 (12) ŵ = 0.45 mm−1
c = 15.6245 (9) ÅT = 296 K
β = 91.250 (6)°Prism, colourless
V = 3752.1 (4) Å30.30 × 0.27 × 0.13 mm
Z = 4
Data collection top
Oxford-Diffraction GEMINI S Ultra
diffractometer		8604 independent reflections
Radiation source: Enhance (Mo) X-ray Source6521 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 16.0774 pixels mm-1θmax = 27.5°, θmin = 2.8°
ω and φ scansh = −15→15
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −26→26
Tmin = 0.876, Tmax = 0.943l = −20→20
34346 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0688P)2]
where P = (Fo2 + 2Fc2)/3
8604 reflections(Δ/σ)max = 0.001
451 parametersΔρmax = 1.01 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C23H25ORu+·C24H20B−V = 3752.1 (4) Å3
Mr = 737.71Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.6754 (8) ŵ = 0.45 mm−1
b = 20.5730 (12) ÅT = 296 K
c = 15.6245 (9) Å0.30 × 0.27 × 0.13 mm
β = 91.250 (6)°
Data collection top
Oxford-Diffraction GEMINI S Ultra
diffractometer		8604 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		6521 reflections with I > 2σ(I)
Tmin = 0.876, Tmax = 0.943Rint = 0.045
34346 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.02Δρmax = 1.01 e Å−3
8604 reflectionsΔρmin = −0.31 e Å−3
451 parameters
Special details top

Experimental. 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
Ru0.84997 (2)−0.09802 (1)0.20184 (1)0.0324 (1)
O11.08769 (19)−0.03654 (13)0.34508 (17)0.0756 (10)
C10.9535 (3)−0.04791 (15)0.10949 (17)0.0482 (9)
C20.9916 (2)−0.11426 (15)0.11576 (17)0.0450 (9)
C30.8987 (2)−0.15534 (13)0.09019 (17)0.0421 (8)
C40.8045 (2)−0.11479 (15)0.06727 (17)0.0442 (9)
C50.8379 (3)−0.04852 (14)0.07874 (17)0.0456 (9)
C61.0233 (4)0.0116 (2)0.1288 (3)0.0896 (16)
C71.1100 (3)−0.1364 (3)0.1403 (2)0.0868 (16)
C80.8996 (4)−0.22797 (17)0.0844 (3)0.0762 (16)
C90.6913 (3)−0.1390 (2)0.0327 (2)0.0752 (14)
C100.7649 (4)0.01049 (19)0.0591 (3)0.0808 (14)
C110.8908 (2)−0.05747 (14)0.33131 (16)0.0405 (8)
C120.9067 (3)−0.12651 (15)0.33336 (18)0.0477 (9)
C130.8181 (3)−0.16832 (15)0.3068 (2)0.0545 (10)
C140.7132 (3)−0.14249 (16)0.2773 (2)0.0544 (10)
C150.6951 (2)−0.07452 (16)0.27371 (18)0.0482 (9)
C160.7850 (2)−0.03171 (13)0.30091 (17)0.0411 (8)
C170.9926 (2)−0.01548 (16)0.35571 (18)0.0499 (10)
C180.9745 (3)0.05050 (16)0.39330 (19)0.0515 (10)
C190.8771 (3)0.06664 (18)0.43805 (19)0.0562 (11)
C200.8658 (3)0.1280 (2)0.4726 (2)0.0742 (14)
C210.9517 (4)0.1732 (2)0.4637 (3)0.0858 (16)
C221.0469 (4)0.1575 (2)0.4208 (4)0.0972 (19)
C231.0602 (3)0.0966 (2)0.3852 (3)0.0757 (16)
C240.5831 (2)0.14110 (11)0.20605 (16)0.0324 (7)
C250.6876 (2)0.14672 (13)0.25259 (18)0.0401 (8)
C260.7888 (2)0.16572 (14)0.2137 (2)0.0514 (10)
C270.7897 (2)0.18102 (14)0.1282 (2)0.0503 (10)
C280.6898 (3)0.17746 (14)0.08089 (19)0.0471 (9)
C290.5894 (2)0.15813 (13)0.11926 (17)0.0386 (8)
C300.3553 (2)0.15999 (12)0.20889 (15)0.0352 (8)
C310.2454 (2)0.13611 (14)0.1953 (2)0.0510 (10)
C320.1541 (3)0.17538 (18)0.1707 (3)0.0676 (13)
C330.1688 (3)0.24065 (17)0.1575 (2)0.0642 (12)
C340.2755 (3)0.26668 (14)0.1697 (2)0.0554 (11)
C350.3669 (2)0.22688 (13)0.19460 (19)0.0446 (9)
C360.4634 (2)0.12033 (12)0.35293 (16)0.0343 (7)
C370.3847 (2)0.15666 (14)0.39862 (18)0.0461 (9)
C380.3842 (3)0.15708 (18)0.4883 (2)0.0631 (11)
C390.4635 (3)0.1221 (2)0.53473 (19)0.0657 (13)
C400.5417 (3)0.08492 (17)0.4927 (2)0.0562 (10)
C410.5402 (2)0.08402 (14)0.40433 (18)0.0446 (9)
C420.43975 (19)0.03810 (12)0.22098 (16)0.0323 (7)
C430.4613 (2)0.01326 (13)0.13928 (17)0.0405 (8)
C440.4402 (2)−0.05134 (15)0.1166 (2)0.0506 (10)
C450.3970 (3)−0.09398 (14)0.1757 (2)0.0560 (10)
C460.3724 (3)−0.07151 (16)0.2559 (2)0.0557 (10)
C470.3925 (2)−0.00675 (14)0.27752 (19)0.0468 (9)
B0.4619 (2)0.11538 (13)0.24744 (18)0.0321 (8)
H6A0.987000.049600.104100.1040*
H6B1.032700.018400.188500.1040*
H6C1.098100.008300.104200.1040*
H7A1.11990−0.139600.200600.1000*
H7B1.16660−0.107500.118500.1000*
H7C1.12480−0.179100.116200.1000*
H8A0.96550−0.243300.056300.0890*
H8B0.83270−0.242900.052400.0890*
H8C0.89710−0.247000.140200.0890*
H9A0.64100−0.148700.078900.0890*
H9B0.65450−0.10670−0.002700.0890*
H9C0.70060−0.17750−0.000300.0890*
H10A0.805900.041300.026300.1000*
H10B0.69730−0.002200.026200.1000*
H10C0.740400.030500.110500.1000*
H120.97920−0.144200.352500.0580*
H130.82930−0.214600.308600.0650*
H140.65290−0.172000.259400.0670*
H150.62300−0.057100.253400.0580*
H160.773700.014300.298400.0500*
H190.818300.035400.444900.0680*
H200.798900.138700.503600.0880*
H210.942700.215600.487400.1040*
H221.107000.189300.414500.1160*
H231.128500.086000.356200.0910*
H250.689100.136900.311300.0480*
H260.857900.168000.247700.0610*
H270.859400.193900.102500.0630*
H280.689500.188500.022100.0570*
H290.521100.156500.085100.0470*
H310.232400.090600.203000.0620*
H320.079900.156900.161700.0840*
H330.105600.267500.140900.0770*
H340.287900.311800.160500.0670*
H350.440200.246000.202000.0530*
H370.328300.181300.368000.0560*
H380.329500.182200.516900.0770*
H390.463600.123800.595200.0800*
H400.596300.059900.524600.0680*
H410.594200.057200.376100.0540*
H430.492700.041100.097700.0470*
H440.45330−0.065500.060300.0590*
H450.38460−0.138200.160900.0680*
H460.34270−0.100600.296300.0690*
H470.373600.007300.333100.0570*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru0.0338 (1)0.0337 (1)0.0298 (1)0.0032 (1)0.0029 (1)0.0022 (1)
O10.0451 (13)0.0924 (19)0.0891 (18)0.0093 (12)−0.0040 (12)−0.0270 (15)
C10.0593 (18)0.0520 (17)0.0337 (14)−0.0123 (14)0.0128 (12)0.0010 (13)
C20.0361 (14)0.0651 (19)0.0339 (14)0.0090 (13)0.0056 (11)0.0071 (13)
C30.0474 (15)0.0443 (15)0.0349 (14)0.0137 (12)0.0059 (11)−0.0021 (12)
C40.0428 (15)0.0570 (18)0.0328 (14)0.0118 (12)−0.0013 (11)−0.0044 (12)
C50.0566 (17)0.0473 (16)0.0333 (14)0.0146 (13)0.0086 (12)0.0062 (12)
C60.119 (3)0.085 (3)0.066 (2)−0.055 (3)0.030 (2)−0.005 (2)
C70.0366 (17)0.160 (4)0.064 (2)0.026 (2)0.0057 (15)0.015 (3)
C80.105 (3)0.049 (2)0.075 (3)0.0209 (19)0.013 (2)−0.0080 (18)
C90.0530 (19)0.109 (3)0.063 (2)0.005 (2)−0.0130 (16)−0.024 (2)
C100.111 (3)0.066 (2)0.066 (2)0.047 (2)0.015 (2)0.0216 (19)
C110.0431 (14)0.0490 (16)0.0293 (13)0.0056 (12)0.0019 (10)−0.0009 (12)
C120.0578 (17)0.0505 (16)0.0347 (14)0.0099 (14)0.0022 (12)0.0079 (13)
C130.072 (2)0.0474 (17)0.0444 (16)−0.0005 (15)0.0111 (15)0.0149 (14)
C140.0547 (18)0.0590 (19)0.0501 (17)−0.0141 (15)0.0158 (14)0.0024 (15)
C150.0344 (14)0.0686 (19)0.0420 (15)0.0026 (13)0.0103 (12)−0.0019 (14)
C160.0430 (15)0.0456 (15)0.0348 (13)0.0078 (12)0.0053 (11)−0.0050 (12)
C170.0451 (16)0.070 (2)0.0345 (14)0.0059 (14)0.0006 (11)−0.0029 (14)
C180.0523 (17)0.0608 (19)0.0410 (16)0.0005 (14)−0.0067 (13)−0.0061 (14)
C190.0588 (19)0.071 (2)0.0386 (16)0.0002 (16)−0.0046 (13)−0.0105 (15)
C200.076 (2)0.090 (3)0.056 (2)0.017 (2)−0.0111 (18)−0.025 (2)
C210.098 (3)0.064 (2)0.094 (3)0.011 (2)−0.029 (3)−0.025 (2)
C220.085 (3)0.072 (3)0.134 (4)−0.017 (2)−0.011 (3)−0.011 (3)
C230.062 (2)0.083 (3)0.082 (3)−0.0110 (19)−0.0005 (19)−0.010 (2)
C240.0333 (12)0.0270 (11)0.0369 (13)0.0009 (9)0.0030 (10)−0.0010 (10)
C250.0373 (14)0.0398 (14)0.0433 (15)0.0013 (11)0.0005 (11)0.0030 (12)
C260.0327 (14)0.0466 (16)0.075 (2)0.0001 (12)0.0008 (13)0.0017 (15)
C270.0414 (15)0.0422 (15)0.068 (2)−0.0007 (12)0.0202 (14)0.0022 (14)
C280.0553 (17)0.0404 (15)0.0463 (16)0.0010 (12)0.0190 (13)0.0019 (13)
C290.0401 (14)0.0387 (14)0.0372 (14)−0.0024 (11)0.0049 (11)0.0012 (11)
C300.0372 (13)0.0360 (13)0.0326 (13)0.0028 (10)0.0041 (10)0.0002 (11)
C310.0379 (15)0.0430 (16)0.072 (2)0.0001 (12)−0.0039 (13)0.0034 (15)
C320.0373 (16)0.066 (2)0.099 (3)0.0059 (15)−0.0105 (17)−0.002 (2)
C330.057 (2)0.062 (2)0.073 (2)0.0272 (17)−0.0106 (16)0.0002 (18)
C340.067 (2)0.0384 (15)0.061 (2)0.0130 (14)0.0057 (15)0.0039 (14)
C350.0447 (15)0.0371 (14)0.0520 (17)0.0013 (11)0.0023 (12)0.0009 (12)
C360.0355 (12)0.0326 (12)0.0350 (13)−0.0090 (10)0.0059 (10)0.0001 (10)
C370.0435 (15)0.0517 (16)0.0434 (15)−0.0060 (12)0.0102 (12)−0.0063 (13)
C380.062 (2)0.079 (2)0.0492 (18)−0.0113 (17)0.0230 (16)−0.0165 (17)
C390.070 (2)0.096 (3)0.0317 (15)−0.026 (2)0.0119 (15)−0.0050 (17)
C400.0614 (19)0.068 (2)0.0391 (15)−0.0120 (15)−0.0020 (14)0.0152 (15)
C410.0514 (16)0.0464 (16)0.0362 (14)−0.0020 (12)0.0033 (12)0.0040 (12)
C420.0266 (11)0.0339 (12)0.0362 (13)0.0017 (9)−0.0016 (9)0.0018 (10)
C430.0401 (14)0.0414 (14)0.0398 (14)0.0044 (11)−0.0008 (11)−0.0036 (12)
C440.0418 (15)0.0509 (17)0.0588 (19)0.0074 (13)−0.0048 (13)−0.0185 (15)
C450.0464 (16)0.0359 (15)0.085 (2)−0.0020 (13)−0.0142 (16)−0.0098 (16)
C460.0550 (18)0.0428 (16)0.069 (2)−0.0151 (14)−0.0025 (15)0.0080 (16)
C470.0513 (16)0.0435 (15)0.0456 (16)−0.0110 (12)0.0045 (12)0.0013 (13)
B0.0320 (14)0.0307 (14)0.0338 (14)0.0008 (10)0.0034 (11)0.0024 (11)
Geometric parameters (Å, º) top
Ru—C12.164 (3)C16—H160.9600
Ru—C22.180 (2)C19—H190.9500
Ru—C32.191 (3)C20—H200.9500
Ru—C42.185 (3)C21—H210.9500
Ru—C52.178 (3)C22—H220.9700
Ru—C112.230 (3)C23—H230.9500
Ru—C122.224 (3)C24—C251.411 (3)
Ru—C132.224 (3)C24—C291.404 (4)
Ru—C142.204 (3)C24—B1.656 (3)
Ru—C152.203 (3)C25—C261.396 (4)
Ru—C162.210 (3)C26—C271.373 (4)
O1—C171.207 (3)C27—C281.369 (4)
C1—C21.438 (4)C28—C291.387 (4)
C1—C51.423 (5)C30—C311.386 (3)
C1—C61.498 (5)C30—C351.401 (4)
C2—C31.425 (4)C30—B1.650 (3)
C2—C71.497 (5)C31—C321.385 (5)
C3—C41.420 (4)C32—C331.370 (5)
C3—C81.497 (4)C33—C341.366 (5)
C4—C51.428 (4)C34—C351.394 (4)
C4—C91.502 (4)C36—C371.393 (4)
C5—C101.511 (5)C36—C411.406 (4)
C11—C121.433 (4)C36—B1.651 (4)
C11—C161.417 (3)C37—C381.401 (4)
C11—C171.512 (4)C38—C391.368 (5)
C12—C131.401 (5)C39—C401.370 (5)
C13—C141.404 (5)C40—C411.381 (4)
C14—C151.415 (5)C42—C431.403 (4)
C15—C161.428 (4)C42—C471.399 (4)
C17—C181.496 (5)C42—B1.662 (4)
C18—C191.388 (5)C43—C441.396 (4)
C18—C231.386 (5)C44—C451.377 (4)
C19—C201.380 (5)C45—C461.372 (4)
C20—C211.377 (6)C46—C471.393 (4)
C21—C221.350 (7)C25—H250.9400
C22—C231.381 (6)C26—H260.9600
C6—H6A0.9700C27—H270.9500
C6—H6B0.9500C28—H280.9500
C6—H6C0.9600C29—H290.9500
C7—H7A0.9500C31—H310.9600
C7—H7B0.9600C32—H320.9500
C7—H7C0.9700C33—H330.9500
C8—H8A0.9500C34—H340.9500
C8—H8B0.9700C35—H350.9500
C8—H8C0.9600C37—H370.9500
C9—H9A0.9600C38—H380.9400
C9—H9B0.9600C39—H390.9500
C9—H9C0.9500C40—H400.9500
C10—H10A0.9500C41—H410.9500
C10—H10B0.9700C43—H430.9500
C10—H10C0.9500C44—H440.9400
C12—H120.9600C45—H450.9500
C13—H130.9600C46—H460.9400
C14—H140.9700C47—H470.9500
C15—H150.9600
O1···H6B2.7600C27···H13iii2.7500
O1···H122.5600C28···H13iii2.8200
O1···H232.5700C29···H13iii3.0000
C1···C32.319 (4)C29···H352.8400
C1···C42.303 (4)C29···H432.6800
C1···C72.617 (6)C30···H292.7700
C1···C102.615 (6)C30···H372.5500
C1···C113.563 (4)C31···H372.9900
C2···C42.297 (3)C31···H23iv3.0700
C2···C52.311 (4)C34···H7Aiii3.0300
C2···C62.623 (5)C35···H372.9100
C2···C82.616 (5)C35···H292.9000
C2···C123.571 (4)C36···H472.5700
C3···C12.319 (4)C36···H252.7500
C3···C52.315 (4)C37···H8Aiii2.7800
C3···C72.601 (4)C38···H8Aiii2.8000
C3···C92.586 (4)C41···H252.5400
C3···C133.543 (4)C41···H472.7200
C4···C12.303 (4)C42···H413.0100
C4···C22.297 (3)C42···H312.6600
C4···C82.591 (5)C42···H152.9400
C4···C102.621 (5)C43···H152.9500
C4···C143.519 (4)C44···H10Bvi2.9300
C4···C153.592 (4)C44···H152.9900
C5···C22.311 (4)C45···H152.9800
C5···C32.315 (4)C45···H7Biv2.8300
C5···C62.599 (6)C46···H152.9400
C5···C92.619 (5)C47···H152.9200
C5···C153.545 (4)C47···H413.0800
C5···C163.556 (4)C47···H312.9600
C7···C45i3.495 (5)H6A···H10A2.4200
C8···C37ii3.467 (5)H6A···C102.7900
C10···C283.563 (5)H6B···C172.7500
C11···C152.463 (3)H6B···O12.7600
C11···C132.460 (4)H6C···H10Av2.5600
C11···C13.563 (4)H6C···C10v3.0700
C11···C142.828 (4)H6C···C73.0300
C12···C172.516 (4)H6C···H7B2.5200
C12···C142.428 (5)H6C···C5v3.0800
C12···C152.831 (4)H7A···C34ii3.0300
C12···C162.459 (4)H7B···C62.9700
C12···C23.571 (4)H7B···C45i2.8300
C13···C152.454 (4)H7B···H6C2.5200
C13···C33.543 (4)H7C···C82.8500
C13···C162.838 (4)H7C···H8A2.4500
C13···C27ii3.504 (4)H8A···C37ii2.7800
C13···C112.460 (4)H8A···H7C2.4500
C14···C112.828 (4)H8A···C73.0500
C14···C122.428 (5)H8A···C38ii2.8000
C14···C43.519 (4)H8B···H9C2.1900
C14···C162.454 (4)H8B···C92.7100
C15···C43.592 (4)H8C···C25ii2.9400
C15···C112.463 (3)H9B···H10B2.2500
C15···C53.545 (4)H9B···C102.8900
C15···C132.454 (4)H9C···C82.8400
C15···C122.831 (4)H9C···H8B2.1900
C16···C172.575 (3)H10A···C63.0300
C16···C193.121 (4)H10A···H6A2.4200
C16···C122.459 (4)H10A···H6Cv2.5600
C16···C132.838 (4)H10B···C44vi2.9300
C16···C53.556 (4)H10B···H44vi2.6000
C16···C142.454 (4)H10B···H9B2.2500
C19···C163.121 (4)H10B···C92.8200
C25···C413.229 (4)H12···H35ii2.6000
C27···C13iii3.504 (4)H12···C21viii3.0300
C28···C103.563 (5)H12···O12.5600
C29···C353.204 (4)H13···C27ii2.7500
C29···C433.352 (4)H13···C28ii2.8200
C31···C373.562 (4)H13···C25ii3.0100
C35···C293.204 (4)H13···C26ii2.8400
C35···C373.502 (4)H13···C29ii3.0000
C37···C353.502 (4)H15···C462.9400
C37···C8iii3.467 (5)H15···C432.9500
C37···C313.562 (4)H15···C472.9200
C41···C473.200 (4)H15···C422.9400
C41···C253.229 (4)H15···C442.9900
C43···C293.352 (4)H15···C452.9800
C45···C7iv3.495 (5)H16···C252.9900
C47···C413.200 (4)H16···C192.6900
C5···H6Cv3.0800H16···C182.8500
C6···H7B2.9700H16···H192.3800
C6···H10A3.0300H16···H412.6000
C7···H6C3.0300H19···C112.7500
C7···H8A3.0500H19···C162.6600
C8···H9C2.8400H19···H162.3800
C8···H7C2.8500H23···O12.5700
C9···H8B2.7100H23···C31i3.0700
C9···H10B2.8200H25···C362.7500
C9···H29vi3.0800H25···C412.5400
C10···H9B2.8900H25···H412.2300
C10···H6Cv3.0700H29···C302.7700
C10···H6A2.7900H29···C352.9000
C11···H192.7500H29···H432.4100
C11···H162.0700H29···C9vi3.0800
C11···H122.0800H31···C422.6600
C12···H132.0600H31···C472.9600
C13···H122.0600H34···H46ix2.4600
C13···H142.0500H35···C242.7300
C14···H39vii2.9300H35···C292.8400
C14···H132.0600H35···H12iii2.6000
C14···H152.0800H37···C302.5500
C15···H162.0800H37···C312.9900
C15···H142.0800H37···C352.9100
C15···H39vii2.9700H39···C14vii2.9300
C16···H192.6600H39···C15vii2.9700
C16···H152.0800H41···C252.9000
C17···H6B2.7500H41···C423.0100
C18···H162.8500H41···C473.0800
C19···H162.6900H41···H162.6000
C21···H12viii3.0300H41···H252.2300
C24···H352.7300H43···C242.8500
C24···H432.8500H43···C292.6800
C25···H8Ciii2.9400H43···H292.4100
C25···H13iii3.0100H44···H10Bvi2.6000
C25···H412.9000H46···H34x2.4600
C25···H162.9900H47···C362.5700
C26···H13iii2.8400H47···C412.7200
C1—Ru—C238.67 (12)C2—C7—H7C110.00
C1—Ru—C364.34 (10)H7A—C7—H7B109.00
C1—Ru—C463.96 (11)H7A—C7—H7C108.00
C1—Ru—C538.25 (13)H7B—C7—H7C107.00
C1—Ru—C11108.37 (10)C3—C8—H8A112.00
C1—Ru—C12125.61 (12)C3—C8—H8B110.00
C1—Ru—C13155.02 (13)C3—C8—H8C111.00
C1—Ru—C14167.46 (12)H8A—C8—H8B108.00
C1—Ru—C15135.40 (12)H8A—C8—H8C109.00
C1—Ru—C16112.23 (10)H8B—C8—H8C107.00
C2—Ru—C338.06 (10)C4—C9—H9A110.00
C2—Ru—C463.49 (9)C4—C9—H9B111.00
C2—Ru—C564.03 (11)C4—C9—H9C111.00
C2—Ru—C11117.84 (9)H9A—C9—H9B108.00
C2—Ru—C12108.37 (11)H9A—C9—H9C108.00
C2—Ru—C13119.78 (12)H9B—C9—H9C109.00
C2—Ru—C14146.56 (12)C5—C10—H10A111.00
C2—Ru—C15172.00 (10)C5—C10—H10B110.00
C2—Ru—C16143.45 (10)C5—C10—H10C111.00
C3—Ru—C437.87 (10)H10A—C10—H10B108.00
C3—Ru—C563.99 (10)H10A—C10—H10C109.00
C3—Ru—C11150.40 (9)H10B—C10—H10C108.00
C3—Ru—C12121.10 (11)Ru—C12—H12129.00
C3—Ru—C13106.72 (11)C11—C12—H12120.00
C3—Ru—C14113.97 (11)C13—C12—H12120.00
C3—Ru—C15138.96 (10)Ru—C13—H13130.00
C3—Ru—C16171.48 (10)C12—C13—H13120.00
C4—Ru—C538.22 (11)C14—C13—H13120.00
C4—Ru—C11167.09 (11)Ru—C14—H14130.00
C4—Ru—C12155.35 (11)C13—C14—H14119.00
C4—Ru—C13124.47 (11)C15—C14—H14120.00
C4—Ru—C14106.59 (11)Ru—C15—H15129.00
C4—Ru—C15109.90 (9)C14—C15—H15121.00
C4—Ru—C16133.76 (10)C16—C15—H15120.00
C5—Ru—C11129.39 (11)Ru—C16—H16129.00
C5—Ru—C12162.06 (12)C11—C16—H16120.00
C5—Ru—C13161.18 (12)C15—C16—H16120.00
C5—Ru—C14129.25 (13)C18—C19—H19120.00
C5—Ru—C15108.03 (12)C20—C19—H19120.00
C5—Ru—C16108.26 (10)C19—C20—H20120.00
C11—Ru—C1237.53 (11)C21—C20—H20120.00
C11—Ru—C1367.07 (11)C20—C21—H21119.00
C11—Ru—C1479.23 (11)C22—C21—H21121.00
C11—Ru—C1567.49 (9)C21—C22—H22120.00
C11—Ru—C1637.21 (9)C23—C22—H22119.00
C12—Ru—C1336.73 (12)C18—C23—H23120.00
C12—Ru—C1466.49 (12)C22—C23—H23120.00
C12—Ru—C1579.52 (11)C25—C24—C29114.5 (2)
C12—Ru—C1667.38 (11)C25—C24—B124.2 (2)
C13—Ru—C1436.96 (13)C29—C24—B121.4 (2)
C13—Ru—C1567.32 (12)C24—C25—C26121.9 (3)
C13—Ru—C1679.60 (11)C25—C26—C27120.8 (2)
C14—Ru—C1537.46 (12)C26—C27—C28119.3 (2)
C14—Ru—C1667.53 (11)C27—C28—C29120.0 (3)
C15—Ru—C1637.76 (10)C24—C29—C28123.5 (2)
Ru—C1—C271.27 (16)C31—C30—C35114.6 (2)
Ru—C1—C571.42 (17)C31—C30—B123.2 (2)
Ru—C1—C6124.4 (2)C35—C30—B122.0 (2)
C2—C1—C5107.7 (3)C30—C31—C32122.7 (3)
C2—C1—C6126.6 (3)C31—C32—C33121.0 (3)
C5—C1—C6125.7 (3)C32—C33—C34118.7 (3)
Ru—C2—C170.06 (16)C33—C34—C35120.0 (3)
Ru—C2—C371.40 (14)C30—C35—C34123.1 (2)
Ru—C2—C7126.7 (2)C37—C36—C41114.3 (2)
C1—C2—C3108.1 (2)C37—C36—B123.5 (2)
C1—C2—C7126.1 (3)C41—C36—B122.0 (2)
C3—C2—C7125.7 (3)C36—C37—C38122.2 (3)
Ru—C3—C270.55 (15)C37—C38—C39120.6 (3)
Ru—C3—C470.82 (15)C38—C39—C40119.3 (3)
Ru—C3—C8126.0 (2)C39—C40—C41119.5 (3)
C2—C3—C4107.6 (2)C36—C41—C40123.9 (3)
C2—C3—C8127.1 (3)C43—C42—C47114.5 (2)
C4—C3—C8125.3 (3)C43—C42—B123.0 (2)
Ru—C4—C371.31 (15)C47—C42—B122.4 (2)
Ru—C4—C570.64 (15)C42—C43—C44122.9 (2)
Ru—C4—C9126.30 (19)C43—C44—C45120.1 (3)
C3—C4—C5108.7 (2)C44—C45—C46119.0 (3)
C3—C4—C9124.5 (3)C45—C46—C47120.4 (3)
C5—C4—C9126.7 (3)C42—C47—C46123.0 (3)
Ru—C5—C170.33 (16)C26—C25—H25119.00
Ru—C5—C471.14 (15)C24—C25—H25119.00
Ru—C5—C10125.5 (2)C25—C26—H26119.00
C1—C5—C4107.8 (3)C27—C26—H26120.00
C1—C5—C10126.0 (3)C28—C27—H27121.00
C4—C5—C10126.2 (3)C26—C27—H27120.00
Ru—C11—C1271.00 (16)C27—C28—H28120.00
Ru—C11—C1670.62 (15)C29—C28—H28120.00
Ru—C11—C17126.44 (17)C24—C29—H29118.00
C12—C11—C16119.3 (2)C28—C29—H29118.00
C12—C11—C17117.4 (2)C32—C31—H31119.00
C16—C11—C17123.1 (3)C30—C31—H31118.00
Ru—C12—C1171.47 (16)C31—C32—H32120.00
Ru—C12—C1371.64 (18)C33—C32—H32119.00
C11—C12—C13120.5 (3)C32—C33—H33121.00
Ru—C13—C1271.63 (18)C34—C33—H33121.00
Ru—C13—C1470.76 (18)C35—C34—H34120.00
C12—C13—C14119.9 (3)C33—C34—H34120.00
Ru—C14—C1372.28 (19)C30—C35—H35119.00
Ru—C14—C1571.22 (17)C34—C35—H35118.00
C13—C14—C15121.0 (3)C36—C37—H37119.00
Ru—C15—C1471.33 (18)C38—C37—H37119.00
Ru—C15—C1671.39 (14)C39—C38—H38120.00
C14—C15—C16119.3 (2)C37—C38—H38120.00
Ru—C16—C1172.17 (15)C38—C39—H39120.00
Ru—C16—C1570.86 (15)C40—C39—H39121.00
C11—C16—C15119.9 (2)C41—C40—H40121.00
O1—C17—C11118.7 (3)C39—C40—H40120.00
O1—C17—C18121.2 (3)C36—C41—H41118.00
C11—C17—C18120.0 (2)C40—C41—H41118.00
C17—C18—C19122.6 (3)C42—C43—H43119.00
C17—C18—C23118.5 (3)C44—C43—H43118.00
C19—C18—C23118.9 (3)C45—C44—H44120.00
C18—C19—C20120.1 (3)C43—C44—H44120.00
C19—C20—C21120.1 (3)C44—C45—H45120.00
C20—C21—C22119.9 (4)C46—C45—H45121.00
C21—C22—C23121.2 (4)C45—C46—H46119.00
C18—C23—C22119.8 (4)C47—C46—H46121.00
C1—C6—H6A110.00C46—C47—H47118.00
C1—C6—H6B112.00C42—C47—H47119.00
C1—C6—H6C111.00C24—B—C36112.32 (19)
H6A—C6—H6B108.00C24—B—C42109.78 (18)
H6A—C6—H6C107.00C30—B—C42109.23 (18)
H6B—C6—H6C108.00C36—B—C42107.80 (19)
C2—C7—H7A112.00C30—B—C36108.76 (19)
C2—C7—H7B111.00C24—B—C30108.91 (19)
C2—Ru—C1—C5116.9 (2)C3—Ru—C14—C15−140.99 (16)
C2—Ru—C1—C6−122.0 (4)C4—Ru—C14—C13125.88 (18)
C3—Ru—C1—C2−37.10 (15)C4—Ru—C14—C15−101.24 (18)
C3—Ru—C1—C579.84 (17)C5—Ru—C14—C13161.28 (17)
C3—Ru—C1—C6−159.1 (3)C5—Ru—C14—C15−65.9 (2)
C4—Ru—C1—C2−79.37 (17)C11—Ru—C14—C13−65.99 (18)
C4—Ru—C1—C537.57 (16)C11—Ru—C14—C1566.89 (17)
C4—Ru—C1—C6158.6 (3)C12—Ru—C14—C13−28.89 (18)
C5—Ru—C1—C2−116.9 (2)C12—Ru—C14—C15103.99 (19)
C5—Ru—C1—C6121.0 (4)C13—Ru—C14—C15132.9 (3)
C11—Ru—C1—C2111.87 (16)C15—Ru—C14—C13−132.9 (3)
C11—Ru—C1—C5−131.20 (16)C16—Ru—C14—C13−102.99 (19)
C11—Ru—C1—C6−10.2 (3)C16—Ru—C14—C1529.89 (16)
C12—Ru—C1—C274.06 (19)C1—Ru—C15—C14164.21 (18)
C12—Ru—C1—C5−169.01 (16)C1—Ru—C15—C16−64.6 (2)
C12—Ru—C1—C6−48.0 (3)C3—Ru—C15—C1461.2 (2)
C13—Ru—C1—C236.9 (3)C3—Ru—C15—C16−167.59 (16)
C13—Ru—C1—C5153.8 (2)C4—Ru—C15—C1491.54 (19)
C13—Ru—C1—C6−85.1 (4)C4—Ru—C15—C16−137.22 (16)
C15—Ru—C1—C2−171.89 (15)C5—Ru—C15—C14132.00 (18)
C15—Ru—C1—C5−55.0 (2)C5—Ru—C15—C16−96.77 (17)
C15—Ru—C1—C666.1 (3)C11—Ru—C15—C14−102.02 (19)
C16—Ru—C1—C2151.44 (15)C11—Ru—C15—C1629.21 (15)
C16—Ru—C1—C5−91.63 (17)C12—Ru—C15—C14−64.81 (18)
C16—Ru—C1—C629.4 (3)C12—Ru—C15—C1666.42 (17)
C1—Ru—C2—C3−118.1 (2)C13—Ru—C15—C14−28.52 (18)
C1—Ru—C2—C7120.7 (4)C13—Ru—C15—C16102.71 (18)
C3—Ru—C2—C1118.1 (2)C14—Ru—C15—C16131.2 (2)
C3—Ru—C2—C7−121.2 (4)C16—Ru—C15—C14−131.2 (2)
C4—Ru—C2—C180.68 (18)C1—Ru—C16—C11−91.43 (17)
C4—Ru—C2—C3−37.45 (16)C1—Ru—C16—C15136.77 (17)
C4—Ru—C2—C7−158.6 (4)C2—Ru—C16—C11−61.3 (2)
C5—Ru—C2—C137.88 (17)C2—Ru—C16—C15166.88 (18)
C5—Ru—C2—C3−80.26 (17)C4—Ru—C16—C11−166.04 (16)
C5—Ru—C2—C7158.6 (4)C4—Ru—C16—C1562.2 (2)
C11—Ru—C2—C1−84.87 (18)C5—Ru—C16—C11−132.10 (17)
C11—Ru—C2—C3156.99 (15)C5—Ru—C16—C1596.10 (18)
C11—Ru—C2—C735.8 (4)C11—Ru—C16—C15−131.8 (2)
C12—Ru—C2—C1−124.55 (17)C12—Ru—C16—C1129.32 (16)
C12—Ru—C2—C3117.32 (16)C12—Ru—C16—C15−102.49 (19)
C12—Ru—C2—C7−3.9 (4)C13—Ru—C16—C1165.58 (17)
C13—Ru—C2—C1−163.01 (17)C13—Ru—C16—C15−66.22 (18)
C13—Ru—C2—C378.85 (18)C14—Ru—C16—C11102.14 (18)
C13—Ru—C2—C7−42.3 (4)C14—Ru—C16—C15−29.67 (17)
C14—Ru—C2—C1160.5 (2)C15—Ru—C16—C11131.8 (2)
C14—Ru—C2—C342.4 (3)Ru—C1—C2—C361.58 (18)
C14—Ru—C2—C7−78.8 (4)Ru—C1—C2—C7−121.4 (3)
C16—Ru—C2—C1−48.0 (2)C5—C1—C2—Ru−62.5 (2)
C16—Ru—C2—C3−166.14 (16)C5—C1—C2—C3−0.9 (3)
C16—Ru—C2—C772.7 (4)C5—C1—C2—C7176.1 (3)
C1—Ru—C3—C237.69 (17)C6—C1—C2—Ru119.4 (3)
C1—Ru—C3—C4−79.89 (18)C6—C1—C2—C3−179.0 (3)
C1—Ru—C3—C8159.9 (3)C6—C1—C2—C7−2.1 (5)
C2—Ru—C3—C4−117.6 (2)Ru—C1—C5—C4−61.64 (19)
C2—Ru—C3—C8122.2 (3)Ru—C1—C5—C10120.1 (3)
C4—Ru—C3—C2117.6 (2)C2—C1—C5—Ru62.42 (19)
C4—Ru—C3—C8−120.2 (3)C2—C1—C5—C40.8 (3)
C5—Ru—C3—C280.38 (18)C2—C1—C5—C10−177.5 (3)
C5—Ru—C3—C4−37.19 (17)C6—C1—C5—Ru−119.5 (3)
C5—Ru—C3—C8−157.4 (3)C6—C1—C5—C4178.9 (3)
C11—Ru—C3—C2−44.4 (3)C6—C1—C5—C100.7 (5)
C11—Ru—C3—C4−161.97 (19)Ru—C2—C3—C461.46 (18)
C11—Ru—C3—C877.8 (3)Ru—C2—C3—C8−120.9 (3)
C12—Ru—C3—C2−80.00 (19)C1—C2—C3—Ru−60.73 (18)
C12—Ru—C3—C4162.43 (16)C1—C2—C3—C40.7 (3)
C12—Ru—C3—C842.2 (3)C1—C2—C3—C8178.3 (3)
C13—Ru—C3—C2−117.23 (17)C7—C2—C3—Ru122.3 (3)
C13—Ru—C3—C4125.19 (17)C7—C2—C3—C4−176.3 (3)
C13—Ru—C3—C85.0 (3)C7—C2—C3—C81.3 (5)
C14—Ru—C3—C2−156.01 (17)Ru—C3—C4—C561.03 (19)
C14—Ru—C3—C486.42 (18)Ru—C3—C4—C9−121.7 (3)
C14—Ru—C3—C8−33.8 (3)C2—C3—C4—Ru−61.28 (18)
C15—Ru—C3—C2168.32 (17)C2—C3—C4—C5−0.3 (3)
C15—Ru—C3—C450.7 (2)C2—C3—C4—C9177.0 (3)
C15—Ru—C3—C8−69.5 (3)C8—C3—C4—Ru121.1 (3)
C1—Ru—C4—C380.98 (17)C8—C3—C4—C5−177.9 (3)
C1—Ru—C4—C5−37.60 (18)C8—C3—C4—C9−0.7 (5)
C1—Ru—C4—C9−159.5 (3)Ru—C4—C5—C161.11 (19)
C2—Ru—C4—C337.64 (15)Ru—C4—C5—C10−120.7 (3)
C2—Ru—C4—C5−80.94 (19)C3—C4—C5—Ru−61.45 (19)
C2—Ru—C4—C9157.2 (3)C3—C4—C5—C1−0.3 (3)
C3—Ru—C4—C5−118.6 (2)C3—C4—C5—C10177.9 (3)
C3—Ru—C4—C9119.6 (3)C9—C4—C5—Ru121.4 (3)
C5—Ru—C4—C3118.6 (2)C9—C4—C5—C1−177.5 (3)
C5—Ru—C4—C9−121.9 (3)C9—C4—C5—C100.7 (5)
C12—Ru—C4—C3−38.3 (3)Ru—C11—C12—C13−54.4 (2)
C12—Ru—C4—C5−156.9 (3)C16—C11—C12—Ru53.4 (2)
C12—Ru—C4—C981.3 (4)C16—C11—C12—C13−0.9 (4)
C13—Ru—C4—C3−71.68 (19)C17—C11—C12—Ru−121.9 (2)
C13—Ru—C4—C5169.74 (19)C17—C11—C12—C13−176.3 (3)
C13—Ru—C4—C947.9 (3)Ru—C11—C16—C1554.4 (2)
C14—Ru—C4—C3−107.89 (16)C12—C11—C16—Ru−53.6 (2)
C14—Ru—C4—C5133.53 (19)C12—C11—C16—C150.8 (4)
C14—Ru—C4—C911.7 (3)C17—C11—C16—Ru121.5 (2)
C15—Ru—C4—C3−147.27 (16)C17—C11—C16—C15175.8 (2)
C15—Ru—C4—C594.15 (19)Ru—C11—C17—O1−58.8 (4)
C15—Ru—C4—C9−27.7 (3)Ru—C11—C17—C18122.0 (2)
C16—Ru—C4—C3177.58 (14)C12—C11—C17—O127.0 (4)
C16—Ru—C4—C559.0 (2)C12—C11—C17—C18−152.2 (3)
C16—Ru—C4—C9−62.9 (3)C16—C11—C17—O1−148.1 (3)
C1—Ru—C5—C4117.7 (2)C16—C11—C17—C1832.6 (4)
C1—Ru—C5—C10−120.8 (4)Ru—C12—C13—C14−53.8 (3)
C2—Ru—C5—C1−38.29 (17)C11—C12—C13—Ru54.3 (2)
C2—Ru—C5—C479.40 (17)C11—C12—C13—C140.5 (4)
C2—Ru—C5—C10−159.1 (3)Ru—C13—C14—C15−54.1 (3)
C3—Ru—C5—C1−80.83 (18)C12—C13—C14—Ru54.2 (3)
C3—Ru—C5—C436.86 (15)C12—C13—C14—C150.1 (5)
C3—Ru—C5—C10158.4 (3)Ru—C14—C15—C16−54.8 (2)
C4—Ru—C5—C1−117.7 (2)C13—C14—C15—Ru54.6 (3)
C4—Ru—C5—C10121.5 (4)C13—C14—C15—C16−0.3 (4)
C11—Ru—C5—C167.5 (2)Ru—C15—C16—C11−55.0 (2)
C11—Ru—C5—C4−174.81 (14)C14—C15—C16—Ru54.8 (2)
C11—Ru—C5—C10−53.3 (3)C14—C15—C16—C11−0.2 (4)
C14—Ru—C5—C1178.51 (17)O1—C17—C18—C19−153.1 (3)
C14—Ru—C5—C4−63.8 (2)O1—C17—C18—C2324.9 (5)
C14—Ru—C5—C1057.7 (3)C11—C17—C18—C1926.2 (4)
C15—Ru—C5—C1142.81 (17)C11—C17—C18—C23−155.9 (3)
C15—Ru—C5—C4−99.51 (17)C17—C18—C19—C20178.9 (3)
C15—Ru—C5—C1022.0 (3)C23—C18—C19—C200.9 (5)
C16—Ru—C5—C1103.00 (17)C17—C18—C23—C22−178.7 (4)
C16—Ru—C5—C4−139.32 (15)C19—C18—C23—C22−0.6 (6)
C16—Ru—C5—C10−17.8 (3)C18—C19—C20—C21−0.8 (5)
C1—Ru—C11—C12−125.09 (19)C19—C20—C21—C220.3 (6)
C1—Ru—C11—C16102.81 (17)C20—C21—C22—C230.1 (8)
C1—Ru—C11—C17−14.6 (3)C21—C22—C23—C180.1 (8)
C2—Ru—C11—C12−84.1 (2)C29—C24—C25—C26−2.0 (4)
C2—Ru—C11—C16143.79 (16)B—C24—C25—C26176.9 (2)
C2—Ru—C11—C1726.4 (3)C25—C24—C29—C281.5 (4)
C3—Ru—C11—C12−54.9 (3)B—C24—C29—C28−177.4 (2)
C3—Ru—C11—C16172.98 (18)C25—C24—B—C30139.7 (2)
C3—Ru—C11—C1755.6 (3)C25—C24—B—C3619.2 (3)
C5—Ru—C11—C12−162.16 (19)C25—C24—B—C42−100.7 (3)
C5—Ru—C11—C1665.7 (2)C29—C24—B—C30−41.5 (3)
C5—Ru—C11—C17−51.6 (3)C29—C24—B—C36−162.0 (2)
C12—Ru—C11—C16−132.1 (2)C29—C24—B—C4278.1 (3)
C12—Ru—C11—C17110.5 (3)C24—C25—C26—C271.3 (4)
C13—Ru—C11—C1228.62 (19)C25—C26—C27—C280.0 (4)
C13—Ru—C11—C16−103.48 (18)C26—C27—C28—C29−0.5 (4)
C13—Ru—C11—C17139.2 (3)C27—C28—C29—C24−0.3 (4)
C14—Ru—C11—C1265.23 (19)C35—C30—C31—C32−0.8 (4)
C14—Ru—C11—C16−66.88 (17)B—C30—C31—C32173.7 (3)
C14—Ru—C11—C17175.8 (3)C31—C30—C35—C340.7 (4)
C15—Ru—C11—C12102.49 (19)B—C30—C35—C34−173.9 (3)
C15—Ru—C11—C16−29.61 (16)C31—C30—B—C24148.1 (2)
C15—Ru—C11—C17−147.0 (3)C31—C30—B—C36−89.2 (3)
C16—Ru—C11—C12132.1 (2)C31—C30—B—C4228.3 (3)
C16—Ru—C11—C17−117.4 (3)C35—C30—B—C24−37.8 (3)
C1—Ru—C12—C1172.8 (2)C35—C30—B—C3684.9 (3)
C1—Ru—C12—C13−154.75 (19)C35—C30—B—C42−157.7 (2)
C2—Ru—C12—C11112.06 (17)C30—C31—C32—C330.8 (6)
C2—Ru—C12—C13−115.5 (2)C31—C32—C33—C34−0.5 (6)
C3—Ru—C12—C11151.83 (14)C32—C33—C34—C350.4 (5)
C3—Ru—C12—C13−75.7 (2)C33—C34—C35—C30−0.5 (5)
C4—Ru—C12—C11178.2 (2)C41—C36—C37—C380.8 (4)
C4—Ru—C12—C13−49.3 (4)B—C36—C37—C38176.4 (3)
C11—Ru—C12—C13132.5 (3)C37—C36—C41—C40−1.9 (4)
C13—Ru—C12—C11−132.5 (3)B—C36—C41—C40−177.6 (3)
C14—Ru—C12—C11−103.41 (19)C37—C36—B—C24121.1 (2)
C14—Ru—C12—C1329.06 (19)C37—C36—B—C300.4 (3)
C15—Ru—C12—C11−66.53 (17)C37—C36—B—C42−117.9 (2)
C15—Ru—C12—C1365.9 (2)C41—C36—B—C24−63.6 (3)
C16—Ru—C12—C11−29.08 (15)C41—C36—B—C30175.8 (2)
C16—Ru—C12—C13103.4 (2)C41—C36—B—C4257.4 (3)
C1—Ru—C13—C1255.2 (3)C36—C37—C38—C391.1 (5)
C1—Ru—C13—C14−172.6 (2)C37—C38—C39—C40−1.9 (6)
C2—Ru—C13—C1280.8 (2)C38—C39—C40—C410.9 (5)
C2—Ru—C13—C14−147.00 (18)C39—C40—C41—C361.2 (5)
C3—Ru—C13—C12119.96 (18)C47—C42—C43—C44−1.6 (3)
C3—Ru—C13—C14−107.83 (18)B—C42—C43—C44−178.5 (2)
C4—Ru—C13—C12157.45 (17)C43—C42—C47—C462.4 (4)
C4—Ru—C13—C14−70.4 (2)B—C42—C47—C46179.3 (2)
C11—Ru—C13—C12−29.21 (18)C43—C42—B—C24−41.0 (3)
C11—Ru—C13—C14103.0 (2)C43—C42—B—C3078.3 (3)
C12—Ru—C13—C14132.2 (3)C43—C42—B—C36−163.7 (2)
C14—Ru—C13—C12−132.2 (3)C47—C42—B—C24142.3 (2)
C15—Ru—C13—C12−103.3 (2)C47—C42—B—C30−98.4 (3)
C15—Ru—C13—C1428.89 (18)C47—C42—B—C3619.6 (3)
C16—Ru—C13—C12−65.92 (19)C42—C43—C44—C45−0.4 (4)
C16—Ru—C13—C1466.28 (18)C43—C44—C45—C461.7 (4)
C2—Ru—C14—C1359.1 (3)C44—C45—C46—C47−1.0 (5)
C2—Ru—C14—C15−168.04 (17)C45—C46—C47—C42−1.2 (5)
C3—Ru—C14—C1386.14 (19)
Symmetry codes: (i) x+1, y, z; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+1/2; (iv) x−1, y, z; (v) −x+2, −y, −z; (vi) −x+1, −y, −z; (vii) −x+1, −y, −z+1; (viii) −x+2, −y, −z+1; (ix) −x+1/2, y+1/2, −z+1/2; (x) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC23H25ORu+·C24H20B−
Mr737.71
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)11.6754 (8), 20.5730 (12), 15.6245 (9)
β (°) 91.250 (6)
V (Å3)3752.1 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.45
Crystal size (mm)0.30 × 0.27 × 0.13
Data collection
DiffractometerOxford-Diffraction GEMINI S Ultra
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.876, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections		34346, 8604, 6521
Rint0.045
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.110, 1.02
No. of reflections8604
No. of parameters451
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.01, −0.31

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).

 

Acknowledgements

We acknowledge support of this work by Griffith University, the Queensland University of Technology, the Université d'Orléans and the Eskitis Institute for Cell and Molecular Therapies. We thank Dr Laurent Bornaghi and Dr Chris Brown for their help and support in this project.

References

First citationAltomare, 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.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationGemel, C., Mereiter, K., Schmid, R. & Kirchner, K. (1996). Organometallics, 15, 532–542.  CSD CrossRef CAS Web of Science Google Scholar
 First citationLoughrey, B. T., Healy, P. C., Parsons, P. G. & Williams, M. L. (2008). Inorg. Chem. 47, 8589–8591.  Web of Science CSD CrossRef PubMed CAS Google Scholar
 First citationLoughrey, B. T., Williams, M. L., Healy, P. C., Innocenti, A., Vullo, D., Supuran, C. T., Parsons, P. G. & Poulsen, S.-A. (2009). J. Biol. Inorg. Chem. 14, 935–945.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationMoncol, J. & Coppens, P. (2004). Private communication (refcode BPHENO12). CCDC, Cambridge, England.  Google Scholar
 First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page m1486
https://doi.org/10.1107/S1600536809042731
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