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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 67| Part 9| September 2011| Page m1231
doi:10.1107/S1600536811031655

(η6-Iso­propyl N-phenyl­carbamate)(η5-penta­methyl­cyclo­penta­dien­yl)ruthenium(II) tetra­phenyl­borate acetone monosolvate

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 2 August 2011; accepted 5 August 2011; online 11 August 2011)

The title complex, [Ru(C10H15)(C10H13NO2)](C24H20B)·C3H6O, is related to the analogous O-methyl complex. The average Ru—C distance to the penta­methyl­cyclo­penta­dienyl (Cp*) group is 2.19 (3) Å, and 2.21 (1) Å to the ortho, meta and para C atoms of the arene ring. The Ru—Cipso bond length of 2.272 (3) Å is significantly longer, reflecting movement of the Ru atom away from the C atoms with electronegative substituents attached. The amide H atom in the cation forms an inter­molecular N—H⋯O hydrogen bond with the carbonyl O atom of the acetone solvent mol­ecule. A C—H⋯O inter­action also occurs.

Related literature

For the synthesis and crystal structures of related compounds, 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., Suparan, C. T., Parsons, P. G. & Poulsen, S. A. (2009). J. Biol. Inorg. Chem. 14, 935-945.], 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)(C10H13NO2)](C24H20B)·C3H6O

  • Mr = 792.79

  • Monoclinic, P 21 /c

  • a = 9.8697 (2) Å

  • b = 28.7953 (7) Å

  • c = 14.3384 (3) Å

  • β = 92.334 (2)°

  • V = 4071.61 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.43 mm−1

  • T = 200 K

  • 0.49 × 0.48 × 0.33 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 = 0.818, Tmax = 0.872

  • 44079 measured reflections

  • 9342 independent reflections

  • 8506 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.126

  • S = 1.15

  • 9342 reflections

  • 478 parameters

  • H-atom parameters constrained

  • Δρmax = 1.18 e Å−3

  • Δρmin = −1.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O3 0.88 2.07 2.890 (4) 154
C6—H6C⋯O1 0.95 2.56 3.512 (5) 174

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: TEXSAN (Molecular Structure Corporation, 2001[Molecular Structure Corporation (2001). TEXSAN for Windows. MSC, The Woodlands, Texas, USA.]) and 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: TEXSAN and 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: 10.1107/S1600536811031655/ng5208sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031655/ng5208Isup2.hkl

checkCIF report


Comment top

As part of our ongoing investigations into the structural chemistry of full-sandwich Cp*Ru(II) η6-arene π-bonded complex salts [Cp*Ru(II)-arene]+X- (Loughrey et al., 2008, 2009, 2010), (Cp* = pentamethylcyclopentadiene) we have synthesized and determined the crystal structure of the title salt [Cp*Ru(η6-O-isopropyl N-phenylcarbamate)][BPh4] as its acetone solvate (Figure 1). The crystal lattice for this compound is isostructural with the O-methyl complex (Loughrey et al., 2010) with cell dimensions for this latter complex a 9.8006 (8), b 27.610 (2), c 14.627 (1) Å, β 91.984 (7)°. The major difference in these parameters for the two compounds is the increase in the length of the b axis from 27.620 (2)Å to 28.7953 (7)Å in order to accomodate the increased steric bulk of the iso-propyl group.

In the cation, the average Ru—C distance to the Cp* group is 2.19 (3)Å and 2.21 (1)Å to the ortho, meta and para carbon atoms C12 - C16 of the arene group; in accord with results reported for other Cp*Ru(arene) sandwich complexes (Loughrey et al., 2010 and references therein). The Ru—Cipso bond length of 2.272 (3)Å is, as observed for the other O-alkyl structures, significantly longer, reflecting movement of the Ru atom away from carbon atoms with electronegative substituents attached.

The carbamate group in the arene ligand adopts a trans conformation. The bond distances N1—C17 = 1.387 (5) Å, C17—O1 = 1.207 (5) Å, and C17—O2 = 1.339 (5) Å, are 0.02 - 0.03Å longer than the corresponding distances in the O-methyl, O-ethyl and O-propyl complexes (Loughrey et al., 2010). The –NH—C(=O)—O—C– fragment is twisted out of the plane of the phenyl ring with the C17—O2—C11—C16 torsion angle 9.3 (5)°. The amide proton forms an intermolecular N—H···O hydrogen bond with the carbonyl oxygen of the acetone solvate.

The phenyl ring C11n (n = 1–6) of the [BPh4]- anion and the arene ring are perpendicular to each other and form a head-to-tail polymeric array along the crystallographic a axis, with the ortho and meta protons of the arene ring 3.0Å above and below the plane of ring C11n. The methyl groups of the isopropyl substitutent and acetone solvate interact with the remaining three phenyl rings of the anion through C—H···π interactions (Figure 2).

Related literature top

For the synthesis and crystal structures of related compounds, see: Loughrey et al. (2008, 2009, 2010).

Experimental top

Ruthenium trichloride hydrate (0.20 g,0.76 mmol) was transfered into a reaction vessel using iso-propanol (20 ml) and the solution heated at reflux until all starting material had dissolved. Phenylisocyanate (0.09 µL, 0.76 mmol) and pentamethylcyclopentadiene (0.30 ml, 1.88 mmol) were added to the reaction mixture and the resulting solution heated under reflux conditions for a further 10 h. The solvent was concentrated under vacuum and the remaining residue dissolved in a water/diethyl ether partition mixture (20:20 ml). The aqueous portion was retained and washed with a further three portions of diethyl ether (20 ml). The aqueous layer was then mixed slowly with a solution of NaB(C6H5)4(aq) (5 mL, 0.30 M) resulting in the formation of a white, crystalline precipitate. This material was filtered from solution, redissolved in a minimum quantity of acetone and filtered through a short alumina column (neutral, 150 mesh, acetone eluent). The eluent was concentrated under vacuum and the product recrystallized by allowing the acetone solvent to slowly evaporate. This process yielded crystals of the acetone solvate suitable for X-ray diffraction studies.

Yield = 0.241 g, 43.1%. ESMS (m/z): +ve ion, calcd m/z for [(η5-C5(CH3)5)Ru(η6-C6H5NHCO2CH(CH3)2)]+]: 415.56, found: 416.14 (100%), -ve ion,calcd m/z for B(C6H5)4-: 319.25,found: 319.18 (100%); NMR: 1H (d6DMSO), d 1.27 (d, 6H, CH(CH3)2),1.85 (s, 15H, C5(C5H15)), 3.33 (s,1H, CH(CH3)2),5.74–5.76 (m, 1H, aromatic), 5.87–5.90 (m, 2H, aromatic), 6.24–6.26 (m, 2H, aromatic),6.76–6.80 (m, 4H, B(C6H5)4 para), 6.90–6.94 (m, 8H, B(C6H5)4meta), 7.17–7.19 (m, 8H, B(C6H5)4ortho), 9.78 (s, br, 1H, NH); 13C (d6DMSO),δ 9.81(C5(C5H15)), 21.66 (CH(CH3)2), 30.65 (CH(CH3)2), 77.25(aromatic), 85.24 (aromatic), 85.95 (aromatic), 95.13 (C5(C5H15), 110.01(C-NH), 121.49(4CH, B(C6H5)4-), 125.27 (8CH, B(C6H5)4-), 135.53 (8CH, B(C6H5)4)-, 153.21 (NHCO2), 162.62, 163.11, 163.60, 164.09 (4CH, B(C6H5)4), Signals Split by 11B).

Refinement top

H atoms attached to carbon and nitrogen were constrained as riding atoms, with C–H set to 0.94–96Å and N–H 0.88 Å. Uiso(H) values were set to 1.2Ueq (N, aromatic) and 1.5Ueq (alkyl) of the parent atom.

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: TEXSAN (Molecular Structure Corporation, 2001) and SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 2001) and 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.
[Figure 2] Fig. 2. Crystal packing for (I), viewed down the a axis.
(η6-Isopropyl N-phenylcarbamate)(η5-pentamethylcyclopentadienyl)ruthenium(II) tetraphenylborate acetone monosolvate top
Crystal data top
[Ru(C10H15)(C10H13NO2)](C24H20B)·C3H6OF(000) = 1664
Mr = 792.79Dx = 1.293 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 26954 reflections
a = 9.8697 (2) Åθ = 3.2–32.4°
b = 28.7953 (7) ŵ = 0.43 mm−1
c = 14.3384 (3) ÅT = 200 K
β = 92.334 (2)°Block, colourless
V = 4071.61 (15) Å30.49 × 0.48 × 0.33 mm
Z = 4
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		9342 independent reflections
Radiation source: Enhance (Mo) X-ray Source8506 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 16.0774 pixels mm-1θmax = 27.5°, θmin = 3.3°
ω and ϕ scansh = −12→12
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		k = −37→37
Tmin = 0.818, Tmax = 0.872l = −18→18
44079 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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.15 w = 1/[σ2(Fo2) + (0.0522P)2 + 6.7463P]
where P = (Fo2 + 2Fc2)/3
9342 reflections(Δ/σ)max < 0.001
478 parametersΔρmax = 1.18 e Å−3
0 restraintsΔρmin = −1.20 e Å−3
Crystal data top
[Ru(C10H15)(C10H13NO2)](C24H20B)·C3H6OV = 4071.61 (15) Å3
Mr = 792.79Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.8697 (2) ŵ = 0.43 mm−1
b = 28.7953 (7) ÅT = 200 K
c = 14.3384 (3) Å0.49 × 0.48 × 0.33 mm
β = 92.334 (2)°
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		9342 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		8506 reflections with I > 2σ(I)
Tmin = 0.818, Tmax = 0.872Rint = 0.025
44079 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.15Δρmax = 1.18 e Å−3
9342 reflectionsΔρmin = −1.20 e Å−3
478 parameters
Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd. 2010, Version 1.171.34.14 (release 15-03-2010 CrysAlis171 .NET) 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
Ru10.44124 (2)0.20924 (1)0.41049 (1)0.0230 (1)
O10.2194 (3)0.32596 (10)0.3028 (2)0.0573 (10)
O20.3827 (3)0.37946 (9)0.2802 (2)0.0518 (9)
N10.4439 (3)0.30608 (10)0.2804 (2)0.0365 (8)
C10.3702 (3)0.24487 (11)0.53353 (19)0.0333 (9)
C20.5150 (4)0.24541 (11)0.5359 (2)0.0364 (10)
C30.5620 (3)0.19837 (12)0.5389 (2)0.0326 (9)
C40.4463 (3)0.16854 (10)0.5384 (2)0.0300 (8)
C50.3272 (3)0.19730 (11)0.5356 (2)0.0297 (8)
C60.2792 (5)0.28640 (13)0.5325 (3)0.0523 (13)
C70.6027 (5)0.28816 (14)0.5369 (3)0.0576 (14)
C80.7069 (4)0.18270 (17)0.5457 (3)0.0525 (14)
C90.4498 (4)0.11682 (12)0.5442 (3)0.0463 (11)
C100.1840 (4)0.18072 (14)0.5402 (3)0.0447 (11)
C110.4390 (3)0.25776 (11)0.28548 (19)0.0302 (8)
C120.5621 (3)0.23262 (11)0.2926 (2)0.0318 (9)
C130.5626 (3)0.18379 (12)0.2954 (2)0.0379 (10)
C140.4398 (4)0.15916 (12)0.2938 (2)0.0431 (10)
C150.3168 (4)0.18361 (13)0.2906 (2)0.0397 (10)
C160.3153 (3)0.23274 (12)0.2874 (2)0.0344 (9)
C170.3355 (4)0.33617 (13)0.2892 (2)0.0422 (11)
C180.2889 (4)0.41772 (13)0.2965 (3)0.0483 (11)
C190.3843 (4)0.45778 (16)0.3153 (4)0.0649 (18)
C200.1891 (4)0.42725 (15)0.2186 (3)0.0573 (14)
C111−0.0628 (3)0.15255 (9)0.2436 (2)0.0244 (7)
C112−0.0605 (3)0.17988 (10)0.1626 (2)0.0307 (8)
C113−0.0551 (3)0.22842 (11)0.1645 (3)0.0367 (9)
C114−0.0532 (3)0.25171 (11)0.2486 (3)0.0405 (10)
C115−0.0581 (3)0.22646 (12)0.3296 (3)0.0393 (10)
C116−0.0630 (3)0.17789 (11)0.3273 (2)0.0311 (9)
C121−0.1220 (3)0.07389 (10)0.3350 (2)0.0288 (8)
C122−0.0507 (4)0.07272 (13)0.4217 (2)0.0415 (10)
C123−0.1053 (5)0.05479 (15)0.5020 (2)0.0544 (15)
C124−0.2348 (5)0.03813 (15)0.4999 (3)0.0580 (14)
C125−0.3100 (4)0.03905 (14)0.4169 (3)0.0501 (12)
C126−0.2542 (3)0.05708 (11)0.3365 (2)0.0358 (9)
C1310.1017 (3)0.07966 (9)0.2258 (2)0.0250 (7)
C1320.1706 (3)0.09768 (10)0.1506 (2)0.0303 (8)
C1330.3009 (3)0.08441 (11)0.1300 (2)0.0338 (9)
C1340.3705 (3)0.05224 (11)0.1852 (2)0.0356 (10)
C1350.3067 (3)0.03349 (12)0.2595 (3)0.0417 (10)
C1360.1742 (3)0.04664 (11)0.2788 (2)0.0370 (9)
C141−0.1450 (3)0.07536 (9)0.14778 (19)0.0242 (7)
C142−0.2656 (3)0.09578 (11)0.1127 (2)0.0298 (8)
C143−0.3409 (3)0.07764 (13)0.0372 (2)0.0369 (10)
C144−0.2990 (3)0.03742 (13)−0.0059 (2)0.0407 (10)
C145−0.1806 (3)0.01606 (12)0.0265 (2)0.0405 (10)
C146−0.1062 (3)0.03479 (10)0.1019 (2)0.0311 (8)
B1−0.0576 (3)0.09523 (11)0.2396 (2)0.0233 (8)
O30.7186 (3)0.33650 (10)0.3225 (3)0.0645 (10)
C210.7980 (4)0.36894 (13)0.3270 (3)0.0433 (11)
C220.9161 (4)0.36791 (18)0.3934 (3)0.0608 (14)
C230.7796 (6)0.40992 (17)0.2656 (4)0.0714 (19)
H10.530900.312300.275000.0280*
H6A0.193100.277900.553500.0640*
H6B0.318200.309700.572100.0640*
H6C0.269800.298200.470400.0640*
H7A0.680200.283100.577300.0690*
H7B0.631000.294200.475600.0690*
H7C0.552800.313800.558700.0690*
H8A0.711700.151900.569200.0630*
H8B0.743600.183300.484900.0630*
H8C0.757900.202900.585600.0630*
H9A0.364900.105700.565100.0560*
H9B0.464000.104300.483900.0560*
H9C0.520300.107300.586300.0560*
H10A0.136600.199800.582000.0530*
H10B0.140500.182700.479600.0530*
H10C0.183000.149500.560900.0530*
H120.645800.249000.295300.0390*
H130.646100.167600.298300.0460*
H140.439800.126300.294700.0500*
H150.232900.167100.290500.0490*
H160.231300.248800.286300.0400*
H180.242000.411700.351500.0580*
H19A0.469100.447000.341300.0770*
H19B0.400600.474100.258600.0770*
H19C0.346500.479100.358200.0770*
H20A0.215300.454100.184000.0670*
H20B0.183600.401400.176600.0670*
H20C0.101300.432700.241800.0670*
H112−0.062700.164900.103500.0380*
H113−0.051600.245100.108100.0440*
H114−0.049200.284700.249600.0480*
H115−0.058000.242100.387800.0480*
H116−0.067200.161500.384300.0370*
H1220.038800.084800.425800.0500*
H123−0.052800.054500.559100.0660*
H124−0.273300.025500.554300.0700*
H125−0.401400.028100.414200.0610*
H126−0.308300.057800.280300.0440*
H1320.126000.119800.111500.0350*
H1330.343300.097800.077500.0410*
H1340.460400.043100.171600.0430*
H1350.352200.011500.298000.0500*
H1360.132700.032800.330700.0440*
H142−0.297300.123100.141400.0350*
H143−0.422300.092800.015600.0440*
H144−0.350100.02510−0.057900.0500*
H145−0.15080−0.01170−0.002400.0480*
H146−0.025300.019500.122700.0390*
H22A0.888800.359700.454600.0700*
H22B0.982200.346000.374600.0700*
H22C0.958700.398000.397400.0700*
H23A0.801700.437700.299100.0870*
H23B0.837400.407700.213600.0870*
H23C0.687900.411800.242100.0870*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.0275 (1)0.0226 (1)0.0189 (1)−0.0033 (1)0.0001 (1)−0.0046 (1)
O10.0377 (14)0.0517 (16)0.083 (2)−0.0029 (12)0.0079 (13)0.0006 (15)
O20.0437 (14)0.0396 (14)0.0727 (19)0.0004 (11)0.0098 (13)0.0059 (13)
N10.0370 (14)0.0351 (14)0.0374 (15)−0.0007 (11)0.0025 (11)0.0053 (11)
C10.0537 (19)0.0306 (15)0.0156 (13)0.0042 (13)0.0023 (12)−0.0045 (11)
C20.056 (2)0.0370 (16)0.0157 (13)−0.0142 (14)−0.0029 (12)−0.0006 (11)
C30.0344 (16)0.0433 (17)0.0198 (14)−0.0054 (13)−0.0018 (11)0.0024 (12)
C40.0354 (15)0.0325 (15)0.0224 (13)0.0009 (12)0.0039 (11)0.0004 (11)
C50.0337 (15)0.0339 (15)0.0218 (13)0.0018 (12)0.0035 (11)0.0007 (11)
C60.085 (3)0.0369 (19)0.0353 (19)0.0181 (18)0.0075 (19)−0.0045 (14)
C70.083 (3)0.051 (2)0.038 (2)−0.034 (2)−0.0071 (19)−0.0068 (16)
C80.0368 (19)0.079 (3)0.041 (2)−0.0022 (18)−0.0061 (15)0.0107 (19)
C90.056 (2)0.0317 (17)0.052 (2)0.0030 (15)0.0106 (17)0.0082 (15)
C100.0352 (17)0.057 (2)0.0425 (19)−0.0028 (15)0.0084 (14)0.0041 (16)
C110.0414 (16)0.0333 (15)0.0157 (12)−0.0005 (12)−0.0002 (11)−0.0025 (11)
C120.0299 (14)0.0438 (17)0.0221 (13)−0.0040 (12)0.0061 (11)−0.0049 (12)
C130.0440 (18)0.0445 (18)0.0255 (15)0.0113 (14)0.0053 (13)−0.0113 (13)
C140.067 (2)0.0320 (16)0.0302 (16)−0.0056 (15)0.0013 (15)−0.0147 (13)
C150.0436 (18)0.0483 (19)0.0269 (15)−0.0179 (15)−0.0023 (13)−0.0123 (14)
C160.0317 (15)0.0503 (19)0.0208 (14)0.0010 (13)−0.0037 (11)−0.0058 (13)
C170.0410 (18)0.0451 (19)0.0405 (19)−0.0046 (15)0.0002 (14)0.0013 (15)
C180.0427 (19)0.0413 (19)0.062 (2)0.0075 (15)0.0159 (17)0.0035 (17)
C190.047 (2)0.056 (3)0.091 (4)−0.0011 (19)−0.006 (2)0.002 (2)
C200.055 (2)0.052 (2)0.065 (3)−0.0038 (18)0.003 (2)−0.007 (2)
C1110.0164 (11)0.0264 (13)0.0304 (14)0.0021 (9)−0.0002 (10)−0.0038 (11)
C1120.0279 (14)0.0305 (14)0.0339 (15)0.0020 (11)0.0023 (11)−0.0019 (12)
C1130.0305 (15)0.0285 (15)0.0510 (19)0.0019 (12)0.0002 (13)0.0070 (13)
C1140.0281 (15)0.0242 (14)0.069 (2)0.0029 (11)0.0009 (15)−0.0068 (15)
C1150.0344 (16)0.0344 (16)0.049 (2)0.0020 (13)0.0012 (14)−0.0168 (15)
C1160.0260 (14)0.0324 (15)0.0348 (16)0.0005 (11)0.0010 (11)−0.0066 (12)
C1210.0357 (15)0.0238 (13)0.0268 (14)0.0037 (11)0.0011 (11)−0.0030 (11)
C1220.0460 (19)0.0482 (19)0.0300 (16)0.0094 (15)−0.0003 (14)−0.0013 (14)
C1230.071 (3)0.065 (3)0.0272 (17)0.023 (2)0.0030 (16)0.0068 (16)
C1240.084 (3)0.056 (2)0.036 (2)0.017 (2)0.026 (2)0.0142 (17)
C1250.054 (2)0.047 (2)0.051 (2)−0.0047 (17)0.0241 (18)0.0030 (17)
C1260.0411 (17)0.0347 (16)0.0320 (16)−0.0027 (13)0.0084 (13)−0.0018 (12)
C1310.0223 (12)0.0228 (12)0.0297 (14)−0.0014 (10)−0.0013 (10)−0.0065 (10)
C1320.0277 (14)0.0293 (14)0.0337 (15)0.0014 (11)−0.0016 (11)−0.0036 (12)
C1330.0281 (14)0.0338 (15)0.0400 (17)−0.0026 (12)0.0060 (12)−0.0073 (13)
C1340.0228 (14)0.0301 (15)0.054 (2)0.0005 (11)0.0023 (13)−0.0111 (14)
C1350.0330 (16)0.0368 (17)0.055 (2)0.0111 (13)−0.0009 (14)0.0040 (15)
C1360.0309 (15)0.0355 (16)0.0446 (18)0.0046 (12)0.0029 (13)0.0061 (14)
C1410.0213 (12)0.0273 (13)0.0241 (13)−0.0026 (10)0.0040 (10)−0.0025 (10)
C1420.0251 (13)0.0357 (15)0.0285 (14)0.0013 (11)0.0017 (11)−0.0036 (12)
C1430.0251 (14)0.0517 (19)0.0336 (16)−0.0005 (13)−0.0018 (12)−0.0033 (14)
C1440.0366 (17)0.055 (2)0.0302 (16)−0.0106 (15)−0.0033 (13)−0.0133 (15)
C1450.0388 (17)0.0419 (18)0.0411 (18)−0.0041 (14)0.0055 (14)−0.0192 (15)
C1460.0250 (13)0.0317 (15)0.0368 (16)−0.0017 (11)0.0031 (11)−0.0086 (12)
B10.0215 (14)0.0245 (14)0.0237 (14)0.0003 (11)0.0001 (11)−0.0023 (11)
O30.0510 (17)0.0503 (16)0.093 (2)−0.0068 (13)0.0117 (16)−0.0071 (16)
C210.0417 (18)0.0432 (19)0.046 (2)0.0065 (15)0.0156 (15)−0.0058 (15)
C220.054 (2)0.079 (3)0.050 (2)0.008 (2)0.0092 (18)−0.011 (2)
C230.094 (4)0.059 (3)0.061 (3)−0.003 (3)0.002 (3)0.010 (2)
Geometric parameters (Å, º) top
Ru1—C12.181 (3)C20—H20A0.9600
Ru1—C22.178 (3)C20—H20B0.9600
Ru1—C32.175 (3)C20—H20C0.9500
Ru1—C42.175 (3)C111—C1121.404 (4)
Ru1—C52.184 (3)C111—C1161.405 (4)
Ru1—C112.272 (3)C111—B11.652 (4)
Ru1—C122.213 (3)C112—C1131.399 (4)
Ru1—C132.204 (3)C113—C1141.379 (6)
Ru1—C142.208 (3)C114—C1151.373 (6)
Ru1—C152.199 (3)C115—C1161.400 (5)
Ru1—C162.222 (3)C121—C1261.393 (4)
O1—C171.207 (5)C121—B11.650 (4)
O2—C171.339 (5)C121—C1221.404 (4)
O2—C181.464 (5)C122—C1231.390 (5)
O3—C211.219 (5)C123—C1241.364 (7)
N1—C111.394 (4)C124—C1251.377 (6)
N1—C171.387 (5)C125—C1261.398 (5)
N1—H10.8800C131—C1361.396 (4)
C1—C51.435 (4)C131—B11.655 (4)
C1—C61.495 (5)C131—C1321.398 (4)
C1—C21.428 (5)C132—C1331.385 (4)
C2—C71.505 (6)C133—C1341.383 (4)
C2—C31.432 (5)C134—C1351.370 (5)
C3—C41.429 (4)C135—C1361.400 (4)
C3—C81.499 (5)C141—C1421.402 (4)
C4—C51.437 (4)C141—C1461.402 (4)
C4—C91.492 (5)C141—B11.647 (4)
C5—C101.496 (5)C142—C1431.390 (4)
C11—C161.419 (4)C143—C1441.384 (5)
C11—C121.414 (4)C144—C1451.384 (4)
C12—C131.407 (5)C145—C1461.391 (4)
C13—C141.404 (5)C112—H1120.9500
C14—C151.403 (5)C113—H1130.9400
C15—C161.416 (5)C114—H1140.9500
C18—C201.484 (6)C115—H1150.9500
C18—C191.506 (6)C116—H1160.9500
C6—H6A0.9500C21—C221.475 (6)
C6—H6B0.9500C21—C231.479 (7)
C6—H6C0.9500C122—H1220.9500
C7—H7A0.9500C123—H1230.9500
C7—H7B0.9500C124—H1240.9500
C7—H7C0.9500C125—H1250.9500
C8—H8B0.9600C126—H1260.9500
C8—H8C0.9500C132—H1320.9500
C8—H8A0.9500C133—H1330.9600
C9—H9B0.9500C134—H1340.9500
C9—H9C0.9400C135—H1350.9400
C9—H9A0.9600C136—H1360.9500
C10—H10B0.9600C142—H1420.9500
C10—H10C0.9500C143—H1430.9500
C10—H10A0.9500C144—H1440.9500
C12—H120.9500C145—H1450.9500
C13—H130.9500C146—H1460.9500
C14—H140.9500C22—H22A0.9600
C15—H150.9500C22—H22B0.9500
C16—H160.9500C22—H22C0.9600
C18—H180.9500C23—H23A0.9500
C19—H19A0.9500C23—H23B0.9600
C19—H19C0.9600C23—H23C0.9500
C19—H19B0.9600
O1···C162.858 (4)C133···H142.9400
O1···C203.166 (5)C134···H144ix2.8800
O3···C123.386 (4)C134···H142.7200
O3···N12.890 (4)C135···H23Ax3.0600
O1···H162.2400C135···H143.0100
O1···H182.5700C136···H1222.7700
O1···H22Bi2.6600C136···H1463.0200
O1···H20B2.8400C141···H1262.5900
O1···H6C2.5600C141···H1323.0300
O3···H12.0700C141···H1122.7800
O3···H7B2.6800C142···H1122.8300
O3···H122.6400C142···H22Aviii3.0600
N1···O32.890 (4)C142···H1262.6900
C1···C163.566 (4)C143···H134i2.9800
C1···C42.323 (4)C144···H23Aviii3.0900
C1···C72.610 (6)C144···H19Cvii2.7600
C1···C32.317 (4)C145···H19Cvii2.6000
C1···C102.610 (5)C146···H19Cvii2.9400
C2···C52.314 (5)C146···H145ix3.0300
C2···C62.608 (6)H1···H122.1600
C2···C42.316 (4)H1···O32.0700
C2···C123.557 (4)H6A···C102.8100
C2···C82.617 (6)H6A···C113iii2.9800
C3···C133.517 (4)H6A···H10A2.3600
C3···C92.599 (5)H6B···H7C2.3300
C3···C12.317 (4)H6B···C72.9400
C3···C52.316 (4)H6C···C172.9200
C3···C72.617 (5)H6C···O12.5600
C4···C143.516 (4)H7A···C82.9400
C4···C102.614 (5)H7A···C113xi2.8700
C4···C82.602 (5)H7A···H8C2.4300
C4···C12.323 (4)H7A···C112xi2.9900
C4···C22.316 (4)H7B···O32.6800
C5···C92.615 (5)H7C···H6B2.3300
C5···C62.609 (5)H7C···C62.8200
C5···C153.532 (4)H7C···H142xi2.6000
C5···C22.314 (5)H8A···H9C2.3100
C5···C32.316 (4)H8A···C92.7800
C11···C142.842 (5)H8B···H116vi2.4900
C11···C152.455 (5)H8B···C116vi3.0200
C11···C132.456 (5)H8C···C72.9600
C12···O33.386 (4)H8C···H7A2.4300
C12···C142.436 (5)H8C···C113xi2.9000
C12···C23.557 (4)H8C···H113xi2.4100
C12···C162.434 (4)H9A···H20Biii2.4600
C12···N12.419 (4)H9A···C20iii3.0100
C12···C152.802 (5)H9A···C102.8200
C13···C33.517 (4)H9A···H10C2.1900
C13···C112.456 (5)H9B···C125vi3.1000
C13···C162.817 (4)H9C···H8A2.3100
C13···C152.424 (5)H9C···C82.9200
C14···C122.436 (5)H10A···H6A2.3600
C14···C162.449 (5)H10A···H113iii2.4800
C14···C1333.430 (4)H10A···C62.9600
C14···C112.842 (5)H10A···C113iii3.0700
C14···C1343.505 (5)H10B···H1162.4900
C14···C43.516 (4)H10B···C1162.9100
C15···C122.802 (5)H10C···C92.8200
C15···C112.455 (5)H10C···H20Biii2.2100
C15···C1323.464 (5)H10C···H9A2.1900
C15···C132.424 (5)H12···C114vi3.0700
C15···C53.532 (4)H12···C115vi3.0100
C16···N12.468 (4)H12···O32.6400
C16···C13.566 (4)H12···H12.1600
C16···O12.858 (4)H13···C116vi2.9000
C16···C122.434 (4)H13···C111vi3.0400
C16···C142.449 (5)H14···C1353.0100
C16···C132.817 (4)H14···C1342.7200
C19···C145ii3.518 (6)H14···C1332.9400
C20···O13.166 (5)H15···C1163.0000
C6···H7C2.8200H15···C1312.9600
C6···H10A2.9600H15···C1322.8800
C7···H8C2.9600H15···C1113.0000
C7···H6B2.9400H16···O12.2400
C8···H7A2.9400H16···C172.7200
C8···H9C2.9200H16···C1142.8400
C9···H10C2.8200H16···C1153.0200
C9···H8A2.7800H18···O12.5700
C10···H20Biii3.0700H19A···H144xi2.3900
C10···H9A2.8200H19B···H134iv2.5900
C10···H6A2.8100H19B···C126ii3.0800
C11···H162.0700H19B···H20A2.1600
C11···H122.0600H19C···C145ii2.6000
C12···H132.0500H19C···C144ii2.7600
C112···C1323.297 (4)H19C···C146ii2.9400
C112···C1423.218 (4)H20A···C126ii3.0100
C13···H122.0500H20A···H19B2.1600
C13···H142.0500H20A···C125ii3.0100
C14···H152.0500H20B···C172.8600
C14···H132.0500H20B···H10Cv2.2100
C15···H142.0500H20B···C10v3.0700
C15···H162.0600H20B···O12.8400
C116···C1223.317 (5)H20B···H9Av2.4600
C16···H152.0600H22A···C142xi3.0600
C17···H6C2.9200H22A···H112xi2.2800
C17···H162.7200H22B···H114vi2.5300
C17···H20B2.8600H22B···O1vi2.6600
C19···H134iv2.9000H22C···H23A2.3500
C20···H9Av3.0100H23A···H22C2.3500
C21···H114vi3.0900H23A···C144xi3.0900
C122···C1363.172 (5)H23A···C135iv3.0600
C122···C1163.317 (5)H112···C1412.7800
C126···C1423.395 (4)H112···C1323.0600
C132···C153.464 (5)H112···H22Aviii2.2800
C132···C1123.297 (4)H112···C1422.8300
C132···C1463.328 (4)H112···H1322.2700
C133···C143.430 (4)H113···H8Cviii2.4100
C134···C143.505 (5)H113···H10Av2.4800
C136···C1223.172 (5)H114···H22Bi2.5300
C142···C1263.395 (4)H114···C21i3.0900
C142···C1123.218 (4)H116···H1222.5100
C145···C19vii3.518 (6)H116···C1212.6700
C146···C1323.328 (4)H116···C1222.6200
C111···H1422.8200H116···H8Bi2.4900
C111···H1322.8700H116···H10B2.4900
C111···H13i3.0400H122···C1362.7700
C111···H153.0000H122···H1162.5100
C112···H7Aviii2.9900H122···C1312.9600
C112···H1422.8600H122···H1362.2500
C112···H1322.6500H124···H135xii2.5200
C113···H10Av3.0700H126···C1422.6900
C113···H7Aviii2.8700H126···C1412.5900
C113···H8Cviii2.9000H132···C1122.6500
C113···H6Av2.9800H132···C1413.0300
C114···H12i3.0700H132···C1112.8700
C114···H162.8400H132···H1122.2700
C115···H12i3.0100H133···H143vi2.5200
C115···H163.0200H134···C19x2.9000
C116···H10B2.9100H134···H19Bx2.5900
C116···H153.0000H134···C143vi2.9800
C116···H13i2.9000H135···H124xii2.5200
C116···H8Bi3.0200H136···H1222.2500
C121···H1362.7800H136···C1212.7800
C121···H1162.6700H136···C1222.5500
C122···H1362.5500H142···H7Cviii2.6000
C122···H1162.6200H142···C1112.8200
C125···H20Avii3.0100H142···C1122.8600
C125···H9Bi3.1000H143···H133i2.5200
C126···H19Bvii3.0800H144···C134ix2.8800
C126···H20Avii3.0100H144···H19Aviii2.3900
C131···H1222.9600H145···C146ix3.0300
C131···H1462.5700H145···H146ix2.5100
C131···H152.9600H146···H145ix2.5100
C132···H1462.9800H146···C1312.5700
C132···H152.8800H146···C1322.9800
C132···H1123.0600H146···C1363.0200
C1—Ru1—C238.26 (13)C4—C9—H9B109.00
C1—Ru1—C364.28 (11)C4—C9—H9C110.00
C1—Ru1—C464.44 (11)H9A—C9—H9B109.00
C1—Ru1—C538.38 (12)H9A—C9—H9C110.00
C1—Ru1—C11110.84 (11)H9B—C9—H9C110.00
C1—Ru1—C12132.51 (11)C5—C10—H10A109.00
C1—Ru1—C13164.71 (11)C5—C10—H10B109.00
C1—Ru1—C14158.06 (13)C5—C10—H10C110.00
C1—Ru1—C15127.04 (12)H10A—C10—H10B109.00
C1—Ru1—C16108.14 (11)H10A—C10—H10C110.00
C2—Ru1—C338.41 (13)H10B—C10—H10C109.00
C2—Ru1—C464.28 (11)Ru1—C12—H12128.00
C2—Ru1—C564.09 (12)C11—C12—H12119.00
C2—Ru1—C11110.46 (11)C13—C12—H12120.00
C2—Ru1—C12108.23 (12)Ru1—C13—H13129.00
C2—Ru1—C13127.15 (13)C12—C13—H13120.00
C2—Ru1—C14158.37 (14)C14—C13—H13120.00
C2—Ru1—C15164.43 (14)Ru1—C14—H14130.00
C2—Ru1—C16131.88 (12)C13—C14—H14120.00
C3—Ru1—C438.35 (11)C15—C14—H14120.00
C3—Ru1—C564.20 (11)Ru1—C15—H15129.00
C3—Ru1—C11138.06 (11)C14—C15—H15120.00
C3—Ru1—C12113.36 (11)C16—C15—H15119.00
C3—Ru1—C13106.87 (11)Ru1—C16—H16128.00
C3—Ru1—C14122.26 (13)C11—C16—H16120.00
C3—Ru1—C15151.99 (13)C15—C16—H16120.00
C3—Ru1—C16170.28 (13)O2—C18—H18109.00
C4—Ru1—C538.50 (11)C19—C18—H18108.00
C4—Ru1—C11174.61 (11)C20—C18—H18109.00
C4—Ru1—C12144.42 (11)C18—C19—H19A111.00
C4—Ru1—C13117.24 (11)C18—C19—H19B110.00
C4—Ru1—C14106.63 (11)C18—C19—H19C110.00
C4—Ru1—C15118.11 (12)H19A—C19—H19B108.00
C4—Ru1—C16145.74 (11)H19A—C19—H19C108.00
C5—Ru1—C11139.13 (11)H19B—C19—H19C108.00
C5—Ru1—C12170.88 (12)C18—C20—H20A111.00
C5—Ru1—C13151.28 (12)C18—C20—H20B110.00
C5—Ru1—C14122.14 (12)C18—C20—H20C111.00
C5—Ru1—C15107.41 (12)H20A—C20—H20B108.00
C5—Ru1—C16114.21 (11)H20A—C20—H20C108.00
C11—Ru1—C1236.74 (11)H20B—C20—H20C109.00
C11—Ru1—C1366.54 (11)C112—C111—C116114.6 (2)
C11—Ru1—C1478.72 (11)C112—C111—B1122.0 (2)
C11—Ru1—C1566.58 (12)C116—C111—B1123.4 (2)
C11—Ru1—C1636.79 (11)C111—C112—C113123.1 (3)
C12—Ru1—C1337.14 (12)C112—C113—C114120.1 (3)
C12—Ru1—C1466.86 (12)C113—C114—C115118.9 (3)
C12—Ru1—C1578.83 (12)C114—C115—C116120.8 (4)
C12—Ru1—C1666.56 (11)C111—C116—C115122.5 (3)
C13—Ru1—C1437.10 (13)C122—C121—C126114.5 (3)
C13—Ru1—C1566.82 (12)C122—C121—B1123.2 (3)
C13—Ru1—C1679.05 (11)C126—C121—B1122.3 (2)
C14—Ru1—C1537.11 (14)C121—C122—C123123.0 (4)
C14—Ru1—C1667.11 (12)C122—C123—C124120.4 (3)
C15—Ru1—C1637.34 (13)C123—C124—C125118.9 (4)
C17—O2—C18117.4 (3)C124—C125—C126120.2 (4)
C11—N1—C17126.2 (3)C121—C126—C125122.9 (3)
C11—N1—H1104.00C132—C131—C136114.7 (3)
C17—N1—H1130.00C132—C131—B1119.1 (2)
Ru1—C1—C270.74 (17)C136—C131—B1126.0 (2)
C2—C1—C5107.9 (3)C131—C132—C133123.2 (3)
Ru1—C1—C570.90 (17)C132—C133—C134120.5 (3)
Ru1—C1—C6125.5 (2)C133—C134—C135118.4 (3)
C5—C1—C6125.9 (3)C134—C135—C136120.6 (3)
C2—C1—C6126.3 (3)C131—C136—C135122.6 (3)
Ru1—C2—C370.69 (17)C142—C141—C146115.2 (3)
Ru1—C2—C171.01 (18)C142—C141—B1123.4 (2)
C1—C2—C7125.7 (3)C146—C141—B1121.4 (2)
Ru1—C2—C7124.9 (2)C141—C142—C143122.8 (3)
C1—C2—C3108.2 (3)C142—C143—C144120.2 (3)
C3—C2—C7126.0 (3)C143—C144—C145119.1 (3)
Ru1—C3—C8125.9 (2)C144—C145—C146120.0 (3)
C2—C3—C4108.1 (3)C141—C146—C145122.8 (3)
Ru1—C3—C470.85 (16)C113—C112—H112118.00
C4—C3—C8125.4 (3)C111—C112—H112119.00
C2—C3—C8126.4 (3)C112—C113—H113120.00
Ru1—C3—C270.90 (17)C114—C113—H113120.00
Ru1—C4—C370.81 (17)C115—C114—H114121.00
C3—C4—C5107.8 (3)C113—C114—H114120.00
C3—C4—C9125.7 (3)C114—C115—H115120.00
C5—C4—C9126.4 (3)C116—C115—H115120.00
Ru1—C4—C9125.8 (2)C111—C116—H116119.00
Ru1—C4—C571.05 (16)C115—C116—H116119.00
Ru1—C5—C470.45 (16)C22—C21—C23118.4 (4)
Ru1—C5—C170.72 (16)O3—C21—C23121.1 (4)
C1—C5—C10125.9 (3)O3—C21—C22120.5 (4)
C4—C5—C10126.0 (3)C121—C122—H122119.00
C1—C5—C4108.0 (3)C123—C122—H122118.00
Ru1—C5—C10127.3 (2)C122—C123—H123120.00
Ru1—C11—C1269.37 (17)C124—C123—H123120.00
Ru1—C11—N1131.0 (2)C123—C124—H124121.00
N1—C11—C16122.7 (3)C125—C124—H124120.00
Ru1—C11—C1669.71 (17)C126—C125—H125120.00
N1—C11—C12118.9 (3)C124—C125—H125120.00
C12—C11—C16118.4 (3)C125—C126—H126119.00
Ru1—C12—C1371.06 (17)C121—C126—H126118.00
C11—C12—C13121.0 (3)C131—C132—H132119.00
Ru1—C12—C1173.90 (17)C133—C132—H132118.00
C12—C13—C14120.2 (3)C134—C133—H133120.00
Ru1—C13—C1271.79 (17)C132—C133—H133120.00
Ru1—C13—C1471.64 (18)C135—C134—H134121.00
C13—C14—C15119.5 (3)C133—C134—H134121.00
Ru1—C14—C1571.09 (19)C136—C135—H135120.00
Ru1—C14—C1371.26 (18)C134—C135—H135120.00
Ru1—C15—C1672.22 (18)C131—C136—H136119.00
Ru1—C15—C1471.81 (19)C135—C136—H136118.00
C14—C15—C16120.7 (3)C141—C142—H142119.00
Ru1—C16—C1570.44 (18)C143—C142—H142118.00
Ru1—C16—C1173.51 (17)C142—C143—H143120.00
C11—C16—C15120.0 (3)C144—C143—H143120.00
O1—C17—N1127.2 (3)C145—C144—H144121.00
O2—C17—N1107.5 (3)C143—C144—H144120.00
O1—C17—O2125.4 (4)C144—C145—H145120.00
C19—C18—C20112.6 (4)C146—C145—H145120.00
O2—C18—C19102.1 (3)C141—C146—H146119.00
O2—C18—C20115.1 (3)C145—C146—H146118.00
C1—C6—H6A110.00C21—C22—H22C111.00
C1—C6—H6B109.00C21—C22—H22A111.00
C1—C6—H6C109.00C21—C22—H22B111.00
H6A—C6—H6B110.00H22A—C22—H22C108.00
H6A—C6—H6C110.00H22B—C22—H22C108.00
H6B—C6—H6C109.00H22A—C22—H22B108.00
C2—C7—H7A109.00C21—C23—H23A110.00
C2—C7—H7B109.00C21—C23—H23C110.00
C2—C7—H7C110.00H23A—C23—H23B108.00
H7A—C7—H7B109.00C21—C23—H23B110.00
H7A—C7—H7C110.00H23B—C23—H23C108.00
H7B—C7—H7C110.00H23A—C23—H23C109.00
C3—C8—H8A110.00C111—B1—C131107.8 (2)
C3—C8—H8B109.00C111—B1—C141111.0 (2)
C3—C8—H8C110.00C121—B1—C141109.1 (2)
H8A—C8—H8B109.00C131—B1—C141106.2 (2)
H8A—C8—H8C110.00C121—B1—C131113.5 (2)
H8B—C8—H8C109.00C111—B1—C121109.2 (2)
C4—C9—H9A109.00
C2—Ru1—C1—C5−117.7 (2)C2—Ru1—C14—C13−51.8 (4)
C2—Ru1—C1—C6121.4 (4)C2—Ru1—C14—C15176.5 (3)
C3—Ru1—C1—C237.46 (18)C3—Ru1—C14—C13−74.6 (2)
C3—Ru1—C1—C5−80.22 (19)C3—Ru1—C14—C15153.64 (19)
C3—Ru1—C1—C6158.8 (3)C4—Ru1—C14—C13−113.39 (19)
C4—Ru1—C1—C280.19 (19)C4—Ru1—C14—C15114.9 (2)
C4—Ru1—C1—C5−37.50 (17)C5—Ru1—C14—C13−152.41 (18)
C4—Ru1—C1—C6−158.5 (3)C5—Ru1—C14—C1575.8 (2)
C5—Ru1—C1—C2117.7 (2)C11—Ru1—C14—C1365.85 (19)
C5—Ru1—C1—C6−121.0 (4)C11—Ru1—C14—C15−65.9 (2)
C11—Ru1—C1—C2−96.97 (18)C12—Ru1—C14—C1329.30 (18)
C11—Ru1—C1—C5145.35 (17)C12—Ru1—C14—C15−102.5 (2)
C11—Ru1—C1—C624.4 (3)C13—Ru1—C14—C15−131.8 (3)
C12—Ru1—C1—C2−61.5 (2)C15—Ru1—C14—C13131.8 (3)
C12—Ru1—C1—C5−179.17 (16)C16—Ru1—C14—C13102.5 (2)
C12—Ru1—C1—C659.9 (3)C16—Ru1—C14—C15−29.26 (19)
C14—Ru1—C1—C2150.4 (3)C1—Ru1—C15—C14−158.21 (19)
C14—Ru1—C1—C532.7 (4)C1—Ru1—C15—C1669.7 (2)
C14—Ru1—C1—C6−88.2 (4)C3—Ru1—C15—C14−53.1 (3)
C15—Ru1—C1—C2−172.76 (18)C3—Ru1—C15—C16174.9 (2)
C15—Ru1—C1—C569.6 (2)C4—Ru1—C15—C14−80.3 (2)
C15—Ru1—C1—C6−51.4 (3)C4—Ru1—C15—C16147.63 (17)
C16—Ru1—C1—C2−135.98 (18)C5—Ru1—C15—C14−120.6 (2)
C16—Ru1—C1—C5106.34 (18)C5—Ru1—C15—C16107.31 (19)
C16—Ru1—C1—C6−14.6 (3)C11—Ru1—C15—C14102.7 (2)
C1—Ru1—C2—C3118.1 (3)C11—Ru1—C15—C16−29.40 (17)
C1—Ru1—C2—C7−120.9 (4)C12—Ru1—C15—C1466.2 (2)
C3—Ru1—C2—C1−118.1 (3)C12—Ru1—C15—C16−65.82 (19)
C3—Ru1—C2—C7121.0 (4)C13—Ru1—C15—C1429.31 (19)
C4—Ru1—C2—C1−80.65 (19)C13—Ru1—C15—C16−102.8 (2)
C4—Ru1—C2—C337.48 (17)C14—Ru1—C15—C16−132.1 (3)
C4—Ru1—C2—C7158.5 (4)C16—Ru1—C15—C14132.1 (3)
C5—Ru1—C2—C1−37.68 (18)C1—Ru1—C16—C11100.78 (19)
C5—Ru1—C2—C380.44 (19)C1—Ru1—C16—C15−128.0 (2)
C5—Ru1—C2—C7−158.5 (4)C2—Ru1—C16—C1165.5 (2)
C11—Ru1—C2—C198.05 (19)C2—Ru1—C16—C15−163.3 (2)
C11—Ru1—C2—C3−143.82 (18)C4—Ru1—C16—C11171.78 (19)
C11—Ru1—C2—C7−22.8 (4)C4—Ru1—C16—C15−57.0 (3)
C12—Ru1—C2—C1137.00 (18)C5—Ru1—C16—C11141.57 (18)
C12—Ru1—C2—C3−104.87 (19)C5—Ru1—C16—C15−87.2 (2)
C12—Ru1—C2—C716.2 (4)C11—Ru1—C16—C15131.2 (3)
C13—Ru1—C2—C1173.55 (18)C12—Ru1—C16—C11−28.49 (17)
C13—Ru1—C2—C3−68.3 (2)C12—Ru1—C16—C15102.7 (2)
C13—Ru1—C2—C752.7 (4)C13—Ru1—C16—C11−65.26 (19)
C14—Ru1—C2—C1−150.0 (3)C13—Ru1—C16—C1566.0 (2)
C14—Ru1—C2—C3−31.9 (4)C14—Ru1—C16—C11−102.1 (2)
C14—Ru1—C2—C789.2 (4)C14—Ru1—C16—C1529.1 (2)
C16—Ru1—C2—C162.5 (2)C15—Ru1—C16—C11−131.2 (3)
C16—Ru1—C2—C3−179.38 (17)C18—O2—C17—O15.9 (5)
C16—Ru1—C2—C7−58.4 (4)C18—O2—C17—N1−173.9 (3)
C1—Ru1—C3—C2−37.31 (19)C17—O2—C18—C19160.2 (3)
C1—Ru1—C3—C480.62 (18)C17—O2—C18—C20−77.6 (4)
C1—Ru1—C3—C8−159.0 (4)C17—N1—C11—Ru1−81.3 (4)
C2—Ru1—C3—C4117.9 (3)C17—N1—C11—C169.3 (5)
C2—Ru1—C3—C8−121.7 (4)C11—N1—C17—O10.2 (5)
C4—Ru1—C3—C2−117.9 (3)C17—N1—C11—C12−168.2 (3)
C4—Ru1—C3—C8120.4 (4)C11—N1—C17—O2179.9 (3)
C5—Ru1—C3—C2−80.1 (2)C5—C1—C2—C30.3 (3)
C5—Ru1—C3—C437.81 (17)C6—C1—C2—Ru1−120.5 (3)
C5—Ru1—C3—C8158.2 (4)C6—C1—C2—C3178.3 (3)
C11—Ru1—C3—C255.8 (3)C5—C1—C2—C7−178.6 (3)
C11—Ru1—C3—C4173.76 (17)Ru1—C1—C5—C460.9 (2)
C11—Ru1—C3—C8−65.8 (4)Ru1—C1—C5—C10−122.7 (3)
C12—Ru1—C3—C290.2 (2)C2—C1—C5—Ru1−61.43 (19)
C12—Ru1—C3—C4−151.87 (17)C2—C1—C5—C4−0.5 (3)
C12—Ru1—C3—C8−31.5 (4)C2—C1—C5—C10175.9 (3)
C13—Ru1—C3—C2129.3 (2)C6—C1—C5—Ru1120.6 (3)
C13—Ru1—C3—C4−112.80 (18)C6—C1—C2—C7−0.6 (5)
C13—Ru1—C3—C87.6 (4)Ru1—C1—C2—C3−61.2 (2)
C14—Ru1—C3—C2166.7 (2)Ru1—C1—C2—C7119.9 (3)
C14—Ru1—C3—C4−75.4 (2)C5—C1—C2—Ru161.5 (2)
C14—Ru1—C3—C845.0 (4)C6—C1—C5—C4−178.5 (3)
C15—Ru1—C3—C2−158.5 (3)C6—C1—C5—C10−2.1 (5)
C15—Ru1—C3—C4−40.6 (3)C1—C2—C3—C40.0 (3)
C15—Ru1—C3—C879.8 (4)C7—C2—C3—C4178.9 (3)
C1—Ru1—C4—C3−80.17 (19)C1—C2—C3—C8−177.5 (3)
C1—Ru1—C4—C537.38 (17)C7—C2—C3—Ru1−119.7 (3)
C1—Ru1—C4—C9159.2 (3)Ru1—C2—C3—C4−61.4 (2)
C2—Ru1—C4—C3−37.54 (19)Ru1—C2—C3—C8121.1 (3)
C2—Ru1—C4—C580.0 (2)C1—C2—C3—Ru161.4 (2)
C2—Ru1—C4—C9−158.2 (3)C7—C2—C3—C81.4 (5)
C3—Ru1—C4—C5117.6 (2)C2—C3—C4—C9−177.8 (3)
C3—Ru1—C4—C9−120.7 (3)C8—C3—C4—Ru1−121.0 (3)
C5—Ru1—C4—C3−117.6 (2)Ru1—C3—C4—C5−61.8 (2)
C5—Ru1—C4—C9121.8 (3)Ru1—C3—C4—C9120.8 (3)
C12—Ru1—C4—C348.1 (3)C2—C3—C4—Ru161.4 (2)
C12—Ru1—C4—C5165.61 (19)C2—C3—C4—C5−0.3 (3)
C12—Ru1—C4—C9−72.6 (3)C8—C3—C4—C5177.2 (3)
C13—Ru1—C4—C382.9 (2)C8—C3—C4—C9−0.2 (5)
C13—Ru1—C4—C5−159.61 (17)C3—C4—C5—Ru161.6 (2)
C13—Ru1—C4—C9−37.8 (3)C9—C4—C5—Ru1−121.0 (3)
C14—Ru1—C4—C3121.36 (19)C3—C4—C5—C10.5 (3)
C14—Ru1—C4—C5−121.09 (19)C3—C4—C5—C10−175.9 (3)
C14—Ru1—C4—C90.7 (3)Ru1—C4—C5—C1−61.1 (2)
C15—Ru1—C4—C3159.73 (19)Ru1—C4—C5—C10122.5 (3)
C15—Ru1—C4—C5−82.7 (2)C9—C4—C5—C1177.9 (3)
C15—Ru1—C4—C939.0 (3)C9—C4—C5—C101.5 (5)
C16—Ru1—C4—C3−165.1 (2)C16—C11—C12—C134.1 (4)
C16—Ru1—C4—C5−47.5 (3)N1—C11—C12—C13−178.3 (3)
C16—Ru1—C4—C974.3 (3)C16—C11—C12—Ru1−51.3 (2)
C1—Ru1—C5—C4−118.1 (2)Ru1—C11—C12—C1355.4 (2)
C1—Ru1—C5—C10121.0 (4)N1—C11—C12—Ru1126.3 (3)
C2—Ru1—C5—C137.56 (17)C12—C11—C16—C15−3.8 (4)
C2—Ru1—C5—C4−80.54 (19)Ru1—C11—C16—C15−55.0 (2)
C2—Ru1—C5—C10158.5 (3)N1—C11—C16—Ru1−126.4 (3)
C3—Ru1—C5—C180.44 (19)N1—C11—C16—C15178.7 (3)
C3—Ru1—C5—C4−37.66 (17)C12—C11—C16—Ru151.1 (2)
C3—Ru1—C5—C10−158.6 (3)Ru1—C12—C13—C1454.9 (2)
C4—Ru1—C5—C1118.1 (2)C11—C12—C13—C14−1.8 (4)
C4—Ru1—C5—C10−120.9 (4)C11—C12—C13—Ru1−56.7 (2)
C11—Ru1—C5—C1−54.3 (2)C12—C13—C14—Ru1−55.0 (2)
C11—Ru1—C5—C4−172.40 (17)Ru1—C13—C14—C1554.2 (2)
C11—Ru1—C5—C1066.7 (4)C12—C13—C14—C15−0.8 (4)
C13—Ru1—C5—C1158.3 (2)C13—C14—C15—Ru1−54.3 (2)
C13—Ru1—C5—C440.2 (3)Ru1—C14—C15—C1655.3 (3)
C13—Ru1—C5—C10−80.8 (4)C13—C14—C15—C161.1 (4)
C14—Ru1—C5—C1−166.20 (18)C14—C15—C16—C111.3 (4)
C14—Ru1—C5—C475.7 (2)Ru1—C15—C16—C1156.4 (2)
C14—Ru1—C5—C10−45.2 (3)C14—C15—C16—Ru1−55.1 (3)
C15—Ru1—C5—C1−128.39 (18)C116—C111—C112—H112−178.00
C15—Ru1—C5—C4113.51 (18)B1—C111—C112—H1125.00
C15—Ru1—C5—C10−7.4 (3)C112—C111—C116—H116178.00
C16—Ru1—C5—C1−88.98 (19)B1—C111—C116—H116−5.00
C16—Ru1—C5—C4152.92 (17)C111—C112—C113—H113179.00
C16—Ru1—C5—C1032.0 (3)H112—C112—C113—C114179.00
C1—Ru1—C11—N123.4 (3)H112—C112—C113—H113−1.00
C1—Ru1—C11—C12134.33 (18)C112—C113—C114—H114180.00
C1—Ru1—C11—C16−92.70 (19)H113—C113—C114—C115−180.00
C2—Ru1—C11—N1−17.6 (3)H113—C113—C114—H1141.00
C2—Ru1—C11—C1293.3 (2)C113—C114—C115—H115−179.00
C2—Ru1—C11—C16−133.7 (2)H114—C114—C115—C116−180.00
C3—Ru1—C11—N1−50.8 (4)H114—C114—C115—H1150.00
C3—Ru1—C11—C1260.1 (2)C114—C115—C116—H116−179.00
C3—Ru1—C11—C16−166.97 (19)H115—C115—C116—C111−180.00
C5—Ru1—C11—N156.1 (3)H115—C115—C116—H1161.00
C5—Ru1—C11—C12166.98 (18)C126—C121—C122—H122−178.00
C5—Ru1—C11—C16−60.1 (2)B1—C121—C122—H1220.00
C12—Ru1—C11—N1−110.9 (3)C122—C121—C126—H126178.00
C12—Ru1—C11—C16133.0 (3)B1—C121—C126—H1261.00
C13—Ru1—C11—N1−140.3 (3)C121—C122—C123—H123179.00
C13—Ru1—C11—C12−29.39 (17)H122—C122—C123—C124178.00
C13—Ru1—C11—C16103.6 (2)H122—C122—C123—H123−1.00
C14—Ru1—C11—N1−177.2 (3)C122—C123—C124—H124179.00
C14—Ru1—C11—C12−66.26 (19)H123—C123—C124—C125180.00
C14—Ru1—C11—C1666.7 (2)H123—C123—C124—H124−1.00
C15—Ru1—C11—N1146.0 (3)C123—C124—C125—H125−179.00
C15—Ru1—C11—C12−103.2 (2)H124—C124—C125—C126−179.00
C15—Ru1—C11—C1629.82 (19)H124—C124—C125—H1252.00
C16—Ru1—C11—N1116.2 (4)C124—C125—C126—H126−179.00
C16—Ru1—C11—C12−133.0 (3)H125—C125—C126—C121180.00
C1—Ru1—C12—C11−65.1 (2)H125—C125—C126—H126−1.00
C1—Ru1—C12—C13163.13 (17)C136—C131—C132—H132179.00
C2—Ru1—C12—C11−100.03 (19)B1—C131—C132—H1324.00
C2—Ru1—C12—C13128.18 (18)C132—C131—C136—H136−179.00
C3—Ru1—C12—C11−140.88 (18)B1—C131—C136—H136−5.00
C3—Ru1—C12—C1387.33 (19)C131—C132—C133—H133180.00
C4—Ru1—C12—C11−171.06 (18)H132—C132—C133—C134180.00
C4—Ru1—C12—C1357.1 (3)H132—C132—C133—H1330.00
C11—Ru1—C12—C13−131.8 (3)C132—C133—C134—H134−180.00
C13—Ru1—C12—C11131.8 (3)H133—C133—C134—C135−180.00
C14—Ru1—C12—C11102.5 (2)H133—C133—C134—H1340.00
C14—Ru1—C12—C13−29.27 (18)C133—C134—C135—H135180.00
C15—Ru1—C12—C1165.62 (19)H134—C134—C135—C136−179.00
C15—Ru1—C12—C13−66.18 (19)H134—C134—C135—H1351.00
C16—Ru1—C12—C1128.53 (18)C134—C135—C136—H136180.00
C16—Ru1—C12—C13−103.27 (19)H135—C135—C136—C131179.00
C2—Ru1—C13—C12−69.5 (2)H135—C135—C136—H1360.00
C2—Ru1—C13—C14158.69 (18)C146—C141—C142—H142179.00
C3—Ru1—C13—C12−106.61 (18)B1—C141—C142—H1423.00
C3—Ru1—C13—C14121.6 (2)C142—C141—C146—H146180.00
C4—Ru1—C13—C12−146.65 (17)B1—C141—C146—H146−3.00
C4—Ru1—C13—C1481.5 (2)C141—C142—C143—H143−180.00
C5—Ru1—C13—C12−173.5 (2)H142—C142—C143—C144−179.00
C5—Ru1—C13—C1454.7 (3)H142—C142—C143—H1430.00
C11—Ru1—C13—C1229.09 (17)C142—C143—C144—H144−180.00
C11—Ru1—C13—C14−102.7 (2)H143—C143—C144—C145180.00
C12—Ru1—C13—C14−131.8 (3)H143—C143—C144—H1441.00
C14—Ru1—C13—C12131.8 (3)C143—C144—C145—H145180.00
C15—Ru1—C13—C12102.5 (2)H144—C144—C145—C146179.00
C15—Ru1—C13—C14−29.31 (19)H144—C144—C145—H145−2.00
C16—Ru1—C13—C1265.45 (18)C144—C145—C146—H146−180.00
C16—Ru1—C13—C14−66.4 (2)H145—C145—C146—C141−180.00
C1—Ru1—C14—C13−175.8 (3)H145—C145—C146—H1461.00
C1—Ru1—C14—C1552.5 (4)
Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x, −y+1/2, z−1/2; (vi) x+1, y, z; (vii) −x, y−1/2, −z+1/2; (viii) x−1, −y+1/2, z−1/2; (ix) −x, −y, −z; (x) −x+1, y−1/2, −z+1/2; (xi) x+1, −y+1/2, z+1/2; (xii) −x, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.882.072.890 (4)154
C6—H6C···O10.952.563.512 (5)174

Experimental details

Crystal data
Chemical formula[Ru(C10H15)(C10H13NO2)](C24H20B)·C3H6O
Mr792.79
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)9.8697 (2), 28.7953 (7), 14.3384 (3)
β (°) 92.334 (2)
V (Å3)4071.61 (15)
Z4
Radiation typeMo Kα
µ (mm−1)0.43
Crystal size (mm)0.49 × 0.48 × 0.33
Data collection
DiffractometerOxford Diffraction Gemini S Ultra
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.818, 0.872
No. of measured, independent and
observed [I > 2σ(I)] reflections		44079, 9342, 8506
Rint0.025
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.126, 1.15
No. of reflections9342
No. of parameters478
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.18, −1.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), TEXSAN (Molecular Structure Corporation, 2001) and SIR97 (Altomare et al., 1999), TEXSAN (Molecular Structure Corporation, 2001) and SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.882.072.890 (4)154
C6—H6C···O10.952.563.512 (5)174
 

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

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
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 First citationLoughrey, B. T., Williams, M. L., Healy, P. C., Innocenti, A., Vullo, D., Suparan, C. T., Parsons, P. G. & Poulsen, S. A. (2009). J. Biol. Inorg. Chem. 14, 935–945.  CrossRef CAS Google Scholar
 First citationMolecular Structure Corporation (2001). TEXSAN for Windows. MSC, The Woodlands, Texas, USA.  Google Scholar
 First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, 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
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 67| Part 9| September 2011| Page m1231
doi:10.1107/S1600536811031655
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