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

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Crystal structure of {3-[3,5-bis­­(2,6-di­methyl­phen­yl)-1,2-phenyl­ene]-1-(2,6,2′′,6′′-tetra­methyl-1,1′:3′,1′′-ter­phen­yl-5′-yl)imidazol-2-yl­­idene}chlorido­(η6-p-cymene)ruthenium(II) benzene disolvate

aDepartment of Chemistry, Graduate School of Science and Engineering, Tokyo Instiute of Technology, Ookayama, Meguro-ku, Tokyo, 152-8551, Japan
*Correspondence e-mail: goto@chem.titech.ac.jp

Edited by H. Ishida, Okayama University, Japan (Received 20 October 2014; accepted 31 October 2014; online 8 November 2014)

The title compound, [Ru(C47H43N2)Cl(C10H14)]·2C6H6, crystallized with two independent mol­ecules of benzene. One of the N-aryl moieties of the N-heterocyclic carbene (NHC) ligand underwent cyclo­metallation to form a five-membered ruthenacycle. The complex has a three-legged piano-stool structure with two C atoms incorporated in the five-membered ruthenacycle and a Cl atom as legs. The ruthenacycle is essentially coplanar with the imidazole ring of the NHC ligand, making a dihedral angle of 0.85 (8)°.

1. Related literature

For related cyclo­metalated ruthenium complexes bearing NHC and η6-arene ligands, see: Hong et al. (2007[Hong, S. H., Chlenov, A., Day, M. W. & Grubbs, R. H. (2007). Angew. Chem. Int. Ed. 46, 5148-5151.]); Karabıyık et al. (2008[Karabıyık, H., Kılınçarslan, R., Aygün, M., Çetinkaya, B. & García-Granda, S. (2008). Solid State Sci. 10, 104-113.]); Zhang et al. (2009[Zhang, C. Y., Zhao, Y., Li, B., Song, H. B., Xu, S. S. & Wang, B. Q. (2009). Dalton Trans. pp. 5182-5189.]). For Pd complexes bearing the NHC ligands utilized in this study, see: Yamashita et al. (2005[Yamashita, M., Goto, K. & Kawashima, T. (2005). J. Am. Chem. Soc. 127, 7294-7295.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Ru(C47H43N2)Cl(C10H14)]·2C6H6

  • Mr = 1062.78

  • Monoclinic, P 21 /a

  • a = 12.9207 (12) Å

  • b = 19.2867 (17) Å

  • c = 22.977 (2) Å

  • β = 98.6792 (18)°

  • V = 5660.3 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.37 mm−1

  • T = 123 K

  • 0.20 × 0.19 × 0.11 mm

2.2. Data collection

  • Rigaku Saturn CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.]) Tmin = 0.930, Tmax = 0.961

  • 22748 measured reflections

  • 12805 independent reflections

  • 10644 reflections with I > 2σ(I)

  • Rint = 0.016

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.092

  • S = 1.09

  • 12805 reflections

  • 669 parameters

  • H-atom parameters constrained

  • Δρmax = 0.55 e Å−3

  • Δρmin = −0.95 e Å−3

Data collection: CrystalClear (Rigaku, 2009[Rigaku (2009). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Yadokari-XG 2009 (Kabuto et al., 2009[Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn, 51, 218-224.]); software used to prepare material for publication: Yadokari-XG 2009.

Supporting information


Comment top

Transition metal complexes bearing N-heterocyclic carbene (NHC) ligands have been broadly utilized in the catalytic reactions. It has been known that the catalytic performance largely depends on not only the electronic property of the ligand but also steric environment around the metal center. Since these properties can be tuned with changing the substituents on the nitrogen atoms and the carbene ring, a variety of NHCs have been synthesized. In the course of our studies on development of cavity-shaped ligands, we have reported an NHC based on a m-phenylene dendrimer framework and its palladium complexes (Yamashita et al., 2005). Herein, the crystal structure of a ruthenium(II) complex bearing the cavity-shaped NHC is reported, where an aromatic ring on the nitrogen of the NHC ligand underwent cyclometallation to form a five-membered ruthenacycle. Related ruthenacycles bearing an NHC ligand have been reported in the literatures (Hong et al., 2007; Karabıyık et al., 2008; Zhang et al., 2009).

The title compound was synthesized by the reaction of dichloro-(p-cymene)-ruthenium(II) dimer with 1,3-bis(2,2",6,6"-tetramethyl-m-terphenyl-5'-yl)imidazol-2-ylidene. The molecular structure of the title compound is shown in Fig. 1. It was found that one of N-aryl moieties underwent cyclometallation to form a ruthenacycle, which is almost coplanar with the imidazole ring. The bond length of Ru—C(carbene) is 2.0163 (15) Å, which is slightly shorter than that of Ru—C(arene) [2.1192 (14) Å].

Related literature top

For related cyclometalated ruthenium complexes bearing NHC and η6-arene ligands, see: Hong et al. (2007); Karabıyık et al. (2008); Zhang et al. (2009). For Pd complexes bearing the NHC ligands utilized in this study, see: Yamashita et al. (2005).

Experimental top

In a dry box under an argon atmosphere, dichloro-(p-cymeme)-ruthenium(II) (36.3 mg, 0.0593 mmol) was added to a solution of 1,3-bis(2,2",6,6"-tetramethyl-m-terphenyl-5'-yl)imidazol-2-ylidene (75.5 mg, 0.119 mmol) in benzene (1 ml) at room temperature. After the reaction mixture was stirred for 1 h at room temperature, the solution was evaporated in vacuo to afford orange solids, which was put out from the dry box. To the solids was added benzene, and the resulting mixture was subjected to centrifugal separation, and the supernatant was evaporated in vacuo. The resulting orange solids were separated by silica gel chromatography (hexane:ethyl acetate = 3:1) to afford the title compound (66.2 mg, 0.0731 mmol, 61%). Single crystals suitable for X-ray diffraction were obtained by recrystallization from a benzene/hexane solution.

Refinement top

H atoms were treated as riding with C—H = 0.95–1.00 Å and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear (Rigaku, 2009); data reduction: CrystalClear (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari-XG 2009 (Kabuto et al., 2009); software used to prepare material for publication: Yadokari-XG 2009 (Kabuto et al., 2009).

Figures top
Fig. 1. The asymmetric unit of the title compound with 50% probability displacement ellipsoids (arbitrary spheres for H atoms).

Fig. 2. A packing diagram of the title compound viewed along the b axis.
{3-[3,5-Bis(2,6-dimethylphenyl)-1,2-phenylene]-1-(2,6,2'',6''-tetramethyl-1,1':3',1''-terphenyl-5'-yl)imidazol-2-ylidene}chlorido(η6-p-cymene)ruthenium(II) benzene disolvate top
Crystal data top
[Ru(C47H43N2)Cl(C10H14)]·2C6H6Z = 4
Mr = 1062.78F(000) = 2232
Monoclinic, P21/aDx = 1.247 Mg m3
Hall symbol: -P 2yabMo Kα radiation, λ = 0.71075 Å
a = 12.9207 (12) Åθ = 3.1–27.5°
b = 19.2867 (17) ŵ = 0.37 mm1
c = 22.977 (2) ÅT = 123 K
β = 98.6792 (18)°Block, yellow
V = 5660.3 (9) Å30.20 × 0.19 × 0.11 mm
Data collection top
Rigaku Saturn CCD
diffractometer
12805 independent reflections
Radiation source: fine-focus sealed tube10644 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 28.5714 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1614
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
k = 2523
Tmin = 0.930, Tmax = 0.961l = 1929
22748 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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0601P)2 + 0.2421P]
where P = (Fo2 + 2Fc2)/3
12805 reflections(Δ/σ)max = 0.002
669 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.95 e Å3
Crystal data top
[Ru(C47H43N2)Cl(C10H14)]·2C6H6V = 5660.3 (9) Å3
Mr = 1062.78Z = 4
Monoclinic, P21/aMo Kα radiation
a = 12.9207 (12) ŵ = 0.37 mm1
b = 19.2867 (17) ÅT = 123 K
c = 22.977 (2) Å0.20 × 0.19 × 0.11 mm
β = 98.6792 (18)°
Data collection top
Rigaku Saturn CCD
diffractometer
12805 independent reflections
Absorption correction: multi-scan
(REQAB; Jacobson, 1998)
10644 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.961Rint = 0.016
22748 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.09Δρmax = 0.55 e Å3
12805 reflectionsΔρmin = 0.95 e Å3
669 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru10.360440 (8)0.062895 (6)0.706449 (5)0.01560 (5)
Cl10.25369 (3)0.05112 (2)0.783182 (17)0.02670 (9)
C10.43058 (10)0.02365 (8)0.74243 (6)0.0173 (3)
N10.39048 (9)0.08574 (7)0.72351 (6)0.0179 (2)
C20.44408 (11)0.14053 (8)0.75316 (7)0.0232 (3)
H20.42970.18860.74750.028*
C30.52060 (11)0.11182 (9)0.79160 (7)0.0253 (3)
H30.57160.13600.81820.030*
N20.51176 (9)0.04041 (7)0.78549 (6)0.0200 (3)
C40.30243 (10)0.08444 (8)0.67846 (6)0.0173 (3)
C50.27103 (10)0.01743 (8)0.66026 (6)0.0166 (3)
C60.18454 (10)0.01623 (8)0.61421 (6)0.0180 (3)
C70.13737 (11)0.07769 (8)0.59093 (7)0.0196 (3)
H70.07940.07470.56020.023*
C80.17223 (10)0.14278 (8)0.61109 (6)0.0179 (3)
C90.25706 (10)0.14582 (8)0.65617 (6)0.0179 (3)
H90.28340.18920.67140.021*
C100.14148 (11)0.04913 (8)0.58473 (7)0.0197 (3)
C110.17037 (12)0.06778 (8)0.53053 (7)0.0228 (3)
C120.13424 (12)0.13031 (9)0.50442 (7)0.0283 (4)
H120.15440.14370.46790.034*
C130.06951 (12)0.17299 (9)0.53110 (8)0.0317 (4)
H130.04780.21640.51390.038*
C140.03644 (12)0.15230 (9)0.58289 (8)0.0302 (4)
H140.01080.18090.60000.036*
C150.07086 (11)0.09050 (9)0.61051 (7)0.0244 (3)
C160.23756 (13)0.02156 (10)0.49880 (8)0.0310 (4)
H160.27310.04960.47220.046*
H16A0.28980.00170.52760.046*
H16B0.19350.01320.47590.046*
C170.03219 (14)0.06806 (10)0.66587 (9)0.0345 (4)
H170.02120.10070.67510.052*
H17A0.00170.02160.66030.052*
H17B0.09080.06720.69840.052*
C180.12377 (10)0.20829 (8)0.58586 (6)0.0179 (3)
C190.15761 (10)0.23791 (8)0.53645 (7)0.0214 (3)
C200.11532 (11)0.30149 (9)0.51559 (7)0.0252 (3)
H200.13880.32250.48260.030*
C210.03990 (12)0.33414 (8)0.54231 (7)0.0267 (3)
H210.01200.37740.52780.032*
C220.00492 (12)0.30360 (8)0.59040 (7)0.0249 (3)
H220.04760.32600.60840.030*
C230.04557 (11)0.24070 (8)0.61270 (7)0.0207 (3)
C240.23403 (12)0.20088 (10)0.50395 (8)0.0302 (4)
H240.29880.19170.53100.045*
H24A0.24950.22990.47130.045*
H24B0.20350.15690.48840.045*
C250.00462 (13)0.20640 (10)0.66344 (8)0.0309 (4)
H250.05530.21230.69940.046*
H25A0.00600.15680.65510.046*
H25B0.06210.22770.66890.046*
C260.57476 (11)0.00688 (8)0.82359 (6)0.0196 (3)
C270.52753 (11)0.05939 (8)0.85101 (7)0.0208 (3)
H270.45370.06500.84360.025*
C280.58861 (11)0.10408 (8)0.88957 (6)0.0220 (3)
C290.69716 (11)0.09314 (9)0.90096 (7)0.0236 (3)
H290.73940.12250.92810.028*
C300.74393 (11)0.04028 (9)0.87333 (7)0.0226 (3)
C310.68254 (11)0.00313 (8)0.83397 (6)0.0217 (3)
H310.71380.03920.81440.026*
C320.53705 (12)0.16162 (9)0.91814 (7)0.0261 (3)
C330.45692 (14)0.14639 (11)0.95144 (8)0.0367 (4)
C340.40964 (16)0.20071 (13)0.97768 (9)0.0483 (5)
H340.35560.19081.00020.058*
C350.43940 (17)0.26760 (13)0.97159 (9)0.0528 (6)
H350.40700.30380.99040.063*
C360.51653 (16)0.28311 (11)0.93820 (9)0.0437 (5)
H360.53620.33010.93370.052*
C370.56629 (13)0.23046 (10)0.91084 (8)0.0328 (4)
C380.41956 (18)0.07368 (12)0.96011 (11)0.0526 (6)
H380.36090.06270.92920.079*
H38A0.47690.04100.95810.079*
H38B0.39650.07010.99870.079*
C390.64693 (16)0.25022 (11)0.87263 (9)0.0447 (5)
H390.63820.22100.83730.067*
H39A0.63760.29900.86110.067*
H39B0.71730.24350.89470.067*
C400.86022 (11)0.02824 (10)0.88395 (7)0.0286 (4)
C410.90130 (13)0.02343 (11)0.92252 (9)0.0379 (4)
C421.00997 (15)0.03608 (14)0.92929 (11)0.0569 (7)
H421.04060.07020.95640.068*
C431.07192 (14)0.00134 (15)0.89639 (12)0.0632 (8)
H431.14490.00780.90090.076*
C441.03048 (15)0.05101 (14)0.85766 (12)0.0568 (7)
H441.07450.07530.83510.068*
C450.92334 (14)0.06656 (10)0.85087 (10)0.0392 (5)
C460.83268 (18)0.06602 (12)0.95604 (11)0.0526 (6)
H460.78560.09470.92850.079*
H46A0.87640.09600.98410.079*
H46B0.79130.03520.97740.079*
C470.87912 (17)0.12114 (13)0.80810 (10)0.0544 (6)
H470.85230.15960.82940.082*
H47A0.93410.13830.78670.082*
H47B0.82200.10140.78010.082*
C480.49177 (11)0.09900 (8)0.66471 (7)0.0208 (3)
C490.39614 (11)0.11007 (8)0.62670 (6)0.0205 (3)
H490.38490.08840.58910.025*
C500.31645 (11)0.15338 (8)0.64406 (7)0.0214 (3)
H500.25620.16430.61650.026*
C510.32649 (12)0.17976 (8)0.70106 (7)0.0244 (3)
C520.42221 (12)0.16792 (8)0.74033 (7)0.0242 (3)
H520.43030.18570.77930.029*
C530.50315 (11)0.13062 (8)0.72169 (7)0.0228 (3)
H530.56760.12600.74740.027*
C540.58173 (12)0.05819 (9)0.64685 (8)0.0265 (4)
H540.62080.03650.68320.032*
C550.65677 (14)0.10768 (11)0.62205 (10)0.0421 (5)
H550.68160.14290.65160.063*
H55A0.71670.08150.61200.063*
H55B0.62020.13030.58660.063*
C560.54651 (13)0.00056 (10)0.60360 (9)0.0349 (4)
H560.51420.02070.56600.052*
H56A0.60710.02750.59740.052*
H56B0.49540.02880.61940.052*
C570.23787 (14)0.21838 (10)0.72272 (9)0.0363 (4)
H570.17620.21780.69210.055*
H57A0.22090.19590.75830.055*
H57B0.25910.26640.73170.055*
C580.83002 (16)0.17078 (11)0.78449 (10)0.0447 (5)
H580.83620.20390.81540.054*
C590.75182 (15)0.17741 (11)0.73663 (11)0.0462 (5)
H590.70410.21510.73470.055*
C600.74318 (14)0.12989 (12)0.69222 (10)0.0482 (5)
H600.68950.13470.65930.058*
C610.81209 (16)0.07480 (11)0.69479 (10)0.0441 (5)
H610.80560.04160.66390.053*
C620.89048 (15)0.06814 (10)0.74252 (10)0.0398 (5)
H620.93840.03060.74440.048*
C630.89893 (14)0.11590 (12)0.78721 (9)0.0410 (5)
H630.95250.11110.82020.049*
C640.7807 (2)0.28850 (15)0.92676 (11)0.0667 (7)
H640.80770.26250.96080.080*
C650.83034 (18)0.34796 (16)0.91335 (11)0.0654 (7)
H650.89140.36310.93840.079*
C660.79277 (18)0.38599 (14)0.86393 (11)0.0571 (6)
H660.82760.42700.85470.068*
C670.70389 (18)0.36358 (13)0.82818 (10)0.0513 (6)
H670.67710.38920.79390.062*
C680.65344 (18)0.30398 (13)0.84197 (10)0.0524 (6)
H680.59180.28910.81720.063*
C690.6915 (2)0.26635 (14)0.89088 (10)0.0594 (6)
H690.65680.22530.90010.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01645 (7)0.01408 (7)0.01647 (7)0.00035 (4)0.00309 (4)0.00014 (4)
Cl10.02472 (18)0.0330 (2)0.02461 (19)0.00300 (15)0.01080 (14)0.00258 (16)
C10.0160 (6)0.0181 (7)0.0184 (7)0.0004 (5)0.0047 (5)0.0005 (6)
N10.0176 (5)0.0143 (6)0.0214 (6)0.0012 (5)0.0016 (5)0.0002 (5)
C20.0218 (7)0.0170 (8)0.0295 (8)0.0033 (6)0.0006 (6)0.0009 (6)
C30.0224 (7)0.0217 (8)0.0294 (8)0.0051 (6)0.0033 (6)0.0001 (7)
N20.0166 (5)0.0195 (7)0.0229 (6)0.0014 (5)0.0000 (5)0.0011 (5)
C40.0150 (6)0.0187 (7)0.0184 (7)0.0000 (5)0.0028 (5)0.0005 (6)
C50.0144 (6)0.0171 (7)0.0188 (7)0.0016 (5)0.0040 (5)0.0009 (6)
C60.0164 (6)0.0175 (7)0.0199 (7)0.0009 (5)0.0027 (5)0.0021 (6)
C70.0168 (6)0.0189 (8)0.0223 (7)0.0001 (5)0.0007 (5)0.0013 (6)
C80.0167 (6)0.0172 (7)0.0202 (7)0.0013 (5)0.0041 (5)0.0008 (6)
C90.0173 (6)0.0140 (7)0.0224 (7)0.0025 (5)0.0033 (5)0.0019 (6)
C100.0171 (6)0.0162 (7)0.0243 (8)0.0016 (5)0.0017 (5)0.0011 (6)
C110.0218 (7)0.0220 (8)0.0226 (8)0.0037 (6)0.0033 (6)0.0023 (6)
C120.0264 (7)0.0283 (9)0.0272 (8)0.0065 (7)0.0058 (6)0.0081 (7)
C130.0238 (7)0.0217 (9)0.0452 (11)0.0008 (6)0.0089 (7)0.0106 (8)
C140.0190 (7)0.0236 (9)0.0462 (10)0.0043 (6)0.0011 (6)0.0028 (8)
C150.0171 (7)0.0227 (8)0.0330 (9)0.0003 (6)0.0021 (6)0.0020 (7)
C160.0381 (9)0.0307 (10)0.0248 (8)0.0040 (7)0.0070 (7)0.0002 (7)
C170.0273 (8)0.0347 (11)0.0444 (11)0.0065 (7)0.0144 (8)0.0053 (8)
C180.0153 (6)0.0151 (7)0.0221 (7)0.0017 (5)0.0007 (5)0.0006 (6)
C190.0165 (6)0.0214 (8)0.0255 (8)0.0034 (6)0.0006 (5)0.0012 (6)
C200.0246 (7)0.0225 (8)0.0270 (8)0.0056 (6)0.0012 (6)0.0070 (7)
C210.0290 (8)0.0147 (8)0.0325 (9)0.0006 (6)0.0079 (6)0.0012 (6)
C220.0227 (7)0.0206 (8)0.0300 (8)0.0043 (6)0.0004 (6)0.0043 (7)
C230.0198 (6)0.0185 (8)0.0231 (7)0.0008 (6)0.0009 (5)0.0024 (6)
C240.0257 (7)0.0361 (10)0.0309 (9)0.0011 (7)0.0109 (6)0.0071 (8)
C250.0318 (8)0.0326 (10)0.0308 (9)0.0061 (7)0.0129 (7)0.0020 (8)
C260.0191 (6)0.0205 (8)0.0182 (7)0.0020 (6)0.0001 (5)0.0002 (6)
C270.0183 (7)0.0249 (9)0.0189 (7)0.0021 (6)0.0018 (5)0.0021 (6)
C280.0251 (7)0.0229 (8)0.0179 (7)0.0030 (6)0.0028 (5)0.0005 (6)
C290.0241 (7)0.0271 (9)0.0186 (7)0.0008 (6)0.0002 (5)0.0036 (6)
C300.0186 (7)0.0267 (8)0.0221 (7)0.0014 (6)0.0019 (5)0.0023 (6)
C310.0202 (7)0.0237 (8)0.0211 (7)0.0001 (6)0.0027 (5)0.0028 (6)
C320.0282 (7)0.0287 (9)0.0194 (7)0.0089 (7)0.0025 (6)0.0039 (6)
C330.0362 (9)0.0454 (12)0.0292 (9)0.0133 (8)0.0074 (7)0.0038 (8)
C340.0471 (11)0.0587 (15)0.0410 (11)0.0199 (10)0.0129 (9)0.0089 (10)
C350.0586 (13)0.0576 (15)0.0404 (11)0.0301 (12)0.0013 (9)0.0178 (11)
C360.0582 (12)0.0301 (11)0.0373 (10)0.0138 (9)0.0108 (9)0.0090 (9)
C370.0388 (9)0.0298 (10)0.0260 (8)0.0062 (7)0.0075 (7)0.0050 (7)
C380.0590 (14)0.0564 (15)0.0507 (14)0.0052 (11)0.0347 (11)0.0036 (11)
C390.0556 (12)0.0301 (11)0.0474 (12)0.0063 (9)0.0046 (9)0.0033 (9)
C400.0173 (7)0.0355 (10)0.0318 (9)0.0001 (7)0.0005 (6)0.0162 (8)
C410.0262 (8)0.0402 (11)0.0429 (11)0.0048 (8)0.0090 (7)0.0143 (9)
C420.0320 (10)0.0599 (15)0.0706 (16)0.0177 (10)0.0189 (10)0.0320 (13)
C430.0163 (8)0.0821 (19)0.0888 (19)0.0036 (10)0.0005 (10)0.0576 (16)
C440.0256 (9)0.0742 (17)0.0743 (17)0.0132 (10)0.0195 (10)0.0453 (14)
C450.0251 (8)0.0465 (12)0.0486 (12)0.0107 (8)0.0138 (8)0.0244 (9)
C460.0505 (12)0.0491 (14)0.0500 (14)0.0040 (10)0.0188 (10)0.0097 (10)
C470.0557 (12)0.0629 (16)0.0493 (13)0.0212 (12)0.0230 (10)0.0023 (11)
C480.0207 (7)0.0190 (8)0.0236 (8)0.0042 (6)0.0065 (5)0.0006 (6)
C490.0268 (7)0.0180 (7)0.0172 (7)0.0051 (6)0.0048 (5)0.0016 (6)
C500.0251 (7)0.0147 (7)0.0240 (8)0.0017 (6)0.0022 (6)0.0043 (6)
C510.0301 (8)0.0145 (8)0.0288 (8)0.0008 (6)0.0052 (6)0.0009 (6)
C520.0318 (8)0.0169 (8)0.0237 (8)0.0036 (6)0.0037 (6)0.0034 (6)
C530.0236 (7)0.0207 (8)0.0237 (7)0.0085 (6)0.0020 (6)0.0003 (6)
C540.0236 (7)0.0279 (9)0.0299 (9)0.0016 (6)0.0097 (6)0.0023 (7)
C550.0354 (9)0.0408 (12)0.0554 (12)0.0127 (8)0.0243 (8)0.0096 (10)
C560.0330 (8)0.0286 (10)0.0464 (11)0.0003 (7)0.0171 (7)0.0088 (8)
C570.0435 (10)0.0251 (10)0.0418 (11)0.0091 (8)0.0104 (8)0.0042 (8)
C580.0510 (11)0.0411 (12)0.0474 (12)0.0113 (10)0.0248 (9)0.0020 (10)
C590.0352 (10)0.0376 (12)0.0700 (15)0.0092 (9)0.0219 (10)0.0166 (11)
C600.0313 (9)0.0533 (14)0.0570 (13)0.0019 (9)0.0033 (9)0.0121 (11)
C610.0462 (11)0.0411 (12)0.0456 (12)0.0048 (9)0.0087 (9)0.0017 (9)
C620.0360 (10)0.0383 (12)0.0486 (13)0.0083 (8)0.0180 (9)0.0152 (9)
C630.0307 (9)0.0577 (14)0.0353 (10)0.0052 (9)0.0072 (7)0.0154 (9)
C640.0867 (18)0.076 (2)0.0354 (12)0.0155 (15)0.0030 (12)0.0201 (13)
C650.0512 (13)0.089 (2)0.0540 (15)0.0042 (13)0.0020 (11)0.0047 (14)
C660.0536 (12)0.0629 (17)0.0596 (15)0.0141 (12)0.0246 (11)0.0122 (12)
C670.0609 (13)0.0560 (15)0.0392 (11)0.0254 (11)0.0150 (10)0.0106 (10)
C680.0587 (13)0.0576 (15)0.0404 (12)0.0143 (11)0.0057 (10)0.0068 (11)
C690.0860 (17)0.0583 (16)0.0365 (12)0.0063 (13)0.0177 (11)0.0002 (11)
Geometric parameters (Å, º) top
Ru1—C12.0163 (15)C34—H340.9500
Ru1—C52.1192 (14)C35—C361.379 (3)
Ru1—C492.1572 (14)C35—H350.9500
Ru1—C482.1852 (14)C36—C371.401 (2)
Ru1—C532.2437 (14)C36—H360.9500
Ru1—C522.2713 (16)C37—C391.509 (3)
Ru1—C502.2754 (15)C38—H380.9800
Ru1—C512.2961 (16)C38—H38A0.9800
Ru1—Cl12.4076 (4)C38—H38B0.9800
C1—N11.350 (2)C39—H390.9800
C1—N21.3675 (18)C39—H39A0.9800
N1—C21.385 (2)C39—H39B0.9800
N1—C41.4180 (17)C40—C411.385 (3)
C2—C31.342 (2)C40—C451.406 (3)
C2—H20.9500C41—C421.411 (2)
C3—N21.387 (2)C41—C461.503 (3)
C3—H30.9500C42—C431.384 (4)
N2—C261.4303 (19)C42—H420.9500
C4—C91.384 (2)C43—C441.361 (4)
C4—C51.399 (2)C43—H430.9500
C5—C61.4186 (18)C44—C451.402 (3)
C6—C71.401 (2)C44—H440.9500
C6—C101.498 (2)C45—C471.494 (3)
C7—C81.389 (2)C46—H460.9800
C7—H70.9500C46—H46A0.9800
C8—C91.3912 (19)C46—H46B0.9800
C8—C181.488 (2)C47—H470.9800
C9—H90.9500C47—H47A0.9800
C10—C111.400 (2)C47—H47B0.9800
C10—C151.408 (2)C48—C491.418 (2)
C11—C121.396 (2)C48—C531.432 (2)
C11—C161.507 (2)C48—C541.511 (2)
C12—C131.381 (2)C49—C501.429 (2)
C12—H120.9500C49—H490.9500
C13—C141.382 (3)C50—C511.393 (2)
C13—H130.9500C50—H500.9500
C14—C151.391 (2)C51—C521.435 (2)
C14—H140.9500C51—C571.512 (2)
C15—C171.499 (2)C52—C531.389 (2)
C16—H160.9800C52—H520.9500
C16—H16A0.9800C53—H530.9500
C16—H16B0.9800C54—C561.515 (2)
C17—H170.9800C54—C551.531 (2)
C17—H17A0.9800C54—H541.0000
C17—H17B0.9800C55—H550.9800
C18—C191.399 (2)C55—H55A0.9800
C18—C231.407 (2)C55—H55B0.9800
C19—C201.397 (2)C56—H560.9800
C19—C241.505 (2)C56—H56A0.9800
C20—C211.380 (2)C56—H56B0.9800
C20—H200.9500C57—H570.9800
C21—C221.387 (2)C57—H57A0.9800
C21—H210.9500C57—H57B0.9800
C22—C231.389 (2)C58—C631.378 (3)
C22—H220.9500C58—C591.382 (3)
C23—C251.504 (2)C58—H580.9500
C24—H240.9800C59—C601.364 (3)
C24—H24A0.9800C59—H590.9500
C24—H24B0.9800C60—C611.382 (3)
C25—H250.9800C60—H600.9500
C25—H25A0.9800C61—C621.382 (3)
C25—H25B0.9800C61—H610.9500
C26—C271.383 (2)C62—C631.372 (3)
C26—C311.3904 (19)C62—H620.9500
C27—C281.393 (2)C63—H630.9500
C27—H270.9500C64—C651.372 (4)
C28—C291.403 (2)C64—C691.380 (4)
C28—C321.496 (2)C64—H640.9500
C29—C301.387 (2)C65—C661.377 (3)
C29—H290.9500C65—H650.9500
C30—C311.390 (2)C66—C671.377 (3)
C30—C401.5035 (19)C66—H660.9500
C31—H310.9500C67—C681.382 (3)
C32—C371.397 (3)C67—H670.9500
C32—C331.408 (2)C68—C691.366 (3)
C33—C341.395 (3)C68—H680.9500
C33—C381.506 (3)C69—H690.9500
C34—C351.359 (3)
C1—Ru1—C577.14 (6)C32—C33—C38122.87 (16)
C1—Ru1—C49123.85 (6)C35—C34—C33121.3 (2)
C5—Ru1—C4993.05 (6)C35—C34—H34119.4
C1—Ru1—C4896.49 (6)C33—C34—H34119.4
C5—Ru1—C48114.45 (5)C34—C35—C36120.16 (19)
C49—Ru1—C4838.10 (5)C34—C35—H35119.9
C1—Ru1—C5396.32 (6)C36—C35—H35119.9
C5—Ru1—C53151.26 (5)C35—C36—C37120.8 (2)
C49—Ru1—C5367.11 (5)C35—C36—H36119.6
C48—Ru1—C5337.69 (5)C37—C36—H36119.6
C1—Ru1—C52119.00 (6)C32—C37—C36118.96 (18)
C5—Ru1—C52163.83 (6)C32—C37—C39122.19 (16)
C49—Ru1—C5278.81 (6)C36—C37—C39118.81 (18)
C48—Ru1—C5267.06 (6)C33—C38—H38109.5
C53—Ru1—C5235.83 (6)C33—C38—H38A109.5
C1—Ru1—C50161.33 (6)H38—C38—H38A109.5
C5—Ru1—C50100.35 (6)C33—C38—H38B109.5
C49—Ru1—C5037.49 (5)H38—C38—H38B109.5
C48—Ru1—C5067.41 (5)H38A—C38—H38B109.5
C53—Ru1—C5076.89 (5)C37—C39—H39109.5
C52—Ru1—C5064.75 (6)C37—C39—H39A109.5
C1—Ru1—C51154.86 (6)H39—C39—H39A109.5
C5—Ru1—C51127.25 (6)C37—C39—H39B109.5
C49—Ru1—C5166.65 (6)H39—C39—H39B109.5
C48—Ru1—C5179.52 (6)H39A—C39—H39B109.5
C53—Ru1—C5165.34 (6)C41—C40—C45121.78 (16)
C52—Ru1—C5136.62 (6)C41—C40—C30119.48 (16)
C50—Ru1—C5135.47 (6)C45—C40—C30118.56 (17)
C1—Ru1—Cl183.88 (4)C40—C41—C42118.3 (2)
C5—Ru1—Cl188.20 (4)C40—C41—C46121.48 (15)
C49—Ru1—Cl1151.81 (4)C42—C41—C46120.2 (2)
C48—Ru1—Cl1156.94 (4)C43—C42—C41119.8 (2)
C53—Ru1—Cl1119.26 (4)C43—C42—H42120.1
C52—Ru1—Cl192.50 (4)C41—C42—H42120.1
C50—Ru1—Cl1114.67 (4)C44—C43—C42121.42 (18)
C51—Ru1—Cl190.36 (4)C44—C43—H43119.3
N1—C1—N2103.80 (13)C42—C43—H43119.3
N1—C1—Ru1118.37 (10)C43—C44—C45120.5 (2)
N2—C1—Ru1137.78 (11)C43—C44—H44119.7
C1—N1—C2112.28 (12)C45—C44—H44119.7
C1—N1—C4116.48 (12)C44—C45—C40118.1 (2)
C2—N1—C4131.23 (13)C44—C45—C47119.8 (2)
C3—C2—N1105.84 (14)C40—C45—C47122.06 (16)
C3—C2—H2127.1C41—C46—H46109.5
N1—C2—H2127.1C41—C46—H46A109.5
C2—C3—N2107.57 (13)H46—C46—H46A109.5
C2—C3—H3126.2C41—C46—H46B109.5
N2—C3—H3126.2H46—C46—H46B109.5
C1—N2—C3110.50 (12)H46A—C46—H46B109.5
C1—N2—C26126.56 (13)C45—C47—H47109.5
C3—N2—C26122.72 (12)C45—C47—H47A109.5
C9—C4—C5126.27 (13)H47—C47—H47A109.5
C9—C4—N1120.21 (13)C45—C47—H47B109.5
C5—C4—N1113.52 (13)H47—C47—H47B109.5
C4—C5—C6113.47 (13)H47A—C47—H47B109.5
C4—C5—Ru1114.45 (10)C49—C48—C53117.32 (13)
C6—C5—Ru1132.08 (11)C49—C48—C54123.09 (14)
C7—C6—C5121.27 (13)C53—C48—C54119.55 (14)
C7—C6—C10115.39 (12)C49—C48—Ru169.88 (8)
C5—C6—C10123.24 (13)C53—C48—Ru173.37 (8)
C8—C7—C6122.45 (13)C54—C48—Ru1129.30 (11)
C8—C7—H7118.8C48—C49—C50120.92 (14)
C6—C7—H7118.8C48—C49—Ru172.02 (8)
C7—C8—C9117.75 (13)C50—C49—Ru175.75 (9)
C7—C8—C18122.76 (13)C48—C49—H49119.5
C9—C8—C18119.48 (13)C50—C49—H49119.5
C4—C9—C8118.78 (14)Ru1—C49—H49124.2
C4—C9—H9120.6C51—C50—C49120.49 (14)
C8—C9—H9120.6C51—C50—Ru173.07 (9)
C11—C10—C15120.35 (15)C49—C50—Ru166.76 (8)
C11—C10—C6119.19 (14)C51—C50—H50119.8
C15—C10—C6120.44 (14)C49—C50—H50119.8
C12—C11—C10119.19 (16)Ru1—C50—H50133.7
C12—C11—C16118.88 (15)C50—C51—C52118.84 (14)
C10—C11—C16121.92 (14)C50—C51—C57121.45 (15)
C13—C12—C11120.66 (16)C52—C51—C57119.67 (15)
C13—C12—H12119.7C50—C51—Ru171.46 (9)
C11—C12—H12119.7C52—C51—Ru170.75 (9)
C12—C13—C14119.77 (16)C57—C51—Ru1127.87 (12)
C12—C13—H13120.1C53—C52—C51120.40 (15)
C14—C13—H13120.1C53—C52—Ru171.00 (9)
C13—C14—C15121.39 (16)C51—C52—Ru172.63 (9)
C13—C14—H14119.3C53—C52—H52119.8
C15—C14—H14119.3C51—C52—H52119.8
C14—C15—C10118.44 (15)Ru1—C52—H52128.9
C14—C15—C17120.66 (15)C52—C53—C48121.62 (14)
C10—C15—C17120.89 (15)C52—C53—Ru173.17 (9)
C11—C16—H16109.5C48—C53—Ru168.94 (8)
C11—C16—H16A109.5C52—C53—H53119.2
H16—C16—H16A109.5C48—C53—H53119.2
C11—C16—H16B109.5Ru1—C53—H53131.7
H16—C16—H16B109.5C48—C54—C56113.15 (13)
H16A—C16—H16B109.5C48—C54—C55109.44 (14)
C15—C17—H17109.5C56—C54—C55110.97 (15)
C15—C17—H17A109.5C48—C54—H54107.7
H17—C17—H17A109.5C56—C54—H54107.7
C15—C17—H17B109.5C55—C54—H54107.7
H17—C17—H17B109.5C54—C55—H55109.5
H17A—C17—H17B109.5C54—C55—H55A109.5
C19—C18—C23120.48 (14)H55—C55—H55A109.5
C19—C18—C8119.89 (13)C54—C55—H55B109.5
C23—C18—C8119.62 (13)H55—C55—H55B109.5
C20—C19—C18118.87 (14)H55A—C55—H55B109.5
C20—C19—C24119.88 (14)C54—C56—H56109.5
C18—C19—C24121.18 (14)C54—C56—H56A109.5
C21—C20—C19120.92 (15)H56—C56—H56A109.5
C21—C20—H20119.5C54—C56—H56B109.5
C19—C20—H20119.5H56—C56—H56B109.5
C20—C21—C22119.85 (15)H56A—C56—H56B109.5
C20—C21—H21120.1C51—C57—H57109.5
C22—C21—H21120.1C51—C57—H57A109.5
C21—C22—C23120.95 (15)H57—C57—H57A109.5
C21—C22—H22119.5C51—C57—H57B109.5
C23—C22—H22119.5H57—C57—H57B109.5
C22—C23—C18118.88 (14)H57A—C57—H57B109.5
C22—C23—C25120.82 (14)C63—C58—C59119.8 (2)
C18—C23—C25120.27 (14)C63—C58—H58120.1
C19—C24—H24109.5C59—C58—H58120.1
C19—C24—H24A109.5C60—C59—C58120.04 (19)
H24—C24—H24A109.5C60—C59—H59120.0
C19—C24—H24B109.5C58—C59—H59120.0
H24—C24—H24B109.5C59—C60—C61120.4 (2)
H24A—C24—H24B109.5C59—C60—H60119.8
C23—C25—H25109.5C61—C60—H60119.8
C23—C25—H25A109.5C60—C61—C62119.7 (2)
H25—C25—H25A109.5C60—C61—H61120.1
C23—C25—H25B109.5C62—C61—H61120.1
H25—C25—H25B109.5C63—C62—C61119.85 (19)
H25A—C25—H25B109.5C63—C62—H62120.1
C27—C26—C31121.54 (14)C61—C62—H62120.1
C27—C26—N2119.76 (12)C62—C63—C58120.25 (19)
C31—C26—N2118.64 (13)C62—C63—H63119.9
C26—C27—C28119.77 (13)C58—C63—H63119.9
C26—C27—H27120.1C65—C64—C69120.1 (2)
C28—C27—H27120.1C65—C64—H64119.9
C27—C28—C29118.69 (14)C69—C64—H64119.9
C27—C28—C32119.41 (13)C64—C65—C66120.8 (2)
C29—C28—C32121.89 (14)C64—C65—H65119.6
C30—C29—C28121.15 (14)C66—C65—H65119.6
C30—C29—H29119.4C67—C66—C65118.9 (3)
C28—C29—H29119.4C67—C66—H66120.6
C29—C30—C31119.70 (13)C65—C66—H66120.6
C29—C30—C40122.21 (14)C66—C67—C68120.3 (2)
C31—C30—C40118.09 (14)C66—C67—H67119.9
C30—C31—C26119.11 (14)C68—C67—H67119.9
C30—C31—H31120.4C69—C68—C67120.5 (2)
C26—C31—H31120.4C69—C68—H68119.8
C37—C32—C33119.85 (16)C67—C68—H68119.8
C37—C32—C28120.38 (15)C68—C69—C64119.4 (3)
C33—C32—C28119.75 (16)C68—C69—H69120.3
C34—C33—C32119.0 (2)C64—C69—H69120.3
C34—C33—C38118.17 (18)
C5—Ru1—C1—N11.61 (10)C41—C40—C45—C440.2 (3)
C49—Ru1—C1—N186.60 (12)C30—C40—C45—C44174.94 (16)
C48—Ru1—C1—N1115.27 (11)C41—C40—C45—C47178.45 (18)
C53—Ru1—C1—N1153.21 (11)C30—C40—C45—C473.3 (3)
C52—Ru1—C1—N1177.40 (10)C1—Ru1—C48—C49139.77 (9)
C50—Ru1—C1—N185.89 (19)C5—Ru1—C48—C4960.98 (10)
C51—Ru1—C1—N1165.58 (11)C53—Ru1—C48—C49128.29 (14)
Cl1—Ru1—C1—N187.93 (10)C52—Ru1—C48—C49101.43 (10)
C5—Ru1—C1—N2178.56 (16)C50—Ru1—C48—C4930.44 (9)
C49—Ru1—C1—N296.45 (16)C51—Ru1—C48—C4965.34 (9)
C48—Ru1—C1—N267.78 (16)Cl1—Ru1—C48—C49130.62 (10)
C53—Ru1—C1—N229.84 (16)C1—Ru1—C48—C5391.94 (10)
C52—Ru1—C1—N20.45 (17)C5—Ru1—C48—C53170.74 (9)
C50—Ru1—C1—N297.2 (2)C49—Ru1—C48—C53128.29 (14)
C51—Ru1—C1—N211.4 (2)C52—Ru1—C48—C5326.86 (9)
Cl1—Ru1—C1—N289.02 (15)C50—Ru1—C48—C5397.85 (10)
N2—C1—N1—C20.20 (16)C51—Ru1—C48—C5362.95 (9)
Ru1—C1—N1—C2178.08 (10)Cl1—Ru1—C48—C532.33 (17)
N2—C1—N1—C4179.11 (12)C1—Ru1—C48—C5422.94 (15)
Ru1—C1—N1—C41.22 (16)C5—Ru1—C48—C5455.86 (15)
C1—N1—C2—C30.40 (17)C49—Ru1—C48—C54116.84 (18)
C4—N1—C2—C3179.58 (15)C53—Ru1—C48—C54114.87 (18)
N1—C2—C3—N20.82 (17)C52—Ru1—C48—C54141.73 (16)
N1—C1—N2—C30.71 (15)C50—Ru1—C48—C54147.27 (16)
Ru1—C1—N2—C3177.95 (12)C51—Ru1—C48—C54177.83 (15)
N1—C1—N2—C26173.97 (13)Cl1—Ru1—C48—C54112.54 (15)
Ru1—C1—N2—C263.3 (2)C53—C48—C49—C502.4 (2)
C2—C3—N2—C10.99 (18)C54—C48—C49—C50175.25 (14)
C2—C3—N2—C26173.93 (13)Ru1—C48—C49—C5060.26 (13)
C1—N1—C4—C9179.43 (12)C53—C48—C49—Ru157.84 (12)
C2—N1—C4—C91.4 (2)C54—C48—C49—Ru1124.50 (15)
C1—N1—C4—C50.36 (18)C1—Ru1—C49—C4850.59 (11)
C2—N1—C4—C5179.51 (14)C5—Ru1—C49—C48127.14 (9)
C9—C4—C5—C60.5 (2)C53—Ru1—C49—C4831.39 (9)
N1—C4—C5—C6178.55 (12)C52—Ru1—C49—C4866.95 (9)
C9—C4—C5—Ru1179.34 (11)C50—Ru1—C49—C48129.78 (13)
N1—C4—C5—Ru11.66 (15)C51—Ru1—C49—C48103.27 (10)
C1—Ru1—C5—C41.75 (10)Cl1—Ru1—C49—C48140.98 (8)
C49—Ru1—C5—C4125.81 (11)C1—Ru1—C49—C50179.63 (8)
C48—Ru1—C5—C493.10 (11)C5—Ru1—C49—C50103.08 (9)
C53—Ru1—C5—C481.29 (16)C48—Ru1—C49—C50129.78 (13)
C52—Ru1—C5—C4175.14 (17)C53—Ru1—C49—C5098.39 (10)
C50—Ru1—C5—C4162.86 (10)C52—Ru1—C49—C5062.83 (9)
C51—Ru1—C5—C4171.46 (9)C51—Ru1—C49—C5026.51 (8)
Cl1—Ru1—C5—C482.38 (10)Cl1—Ru1—C49—C5011.20 (14)
C1—Ru1—C5—C6178.51 (14)C48—C49—C50—C516.8 (2)
C49—Ru1—C5—C654.46 (14)Ru1—C49—C50—C5151.64 (13)
C48—Ru1—C5—C687.16 (14)C48—C49—C50—Ru158.44 (13)
C53—Ru1—C5—C698.98 (16)C1—Ru1—C50—C51136.03 (17)
C52—Ru1—C5—C64.6 (3)C5—Ru1—C50—C51143.53 (9)
C50—Ru1—C5—C617.40 (14)C49—Ru1—C50—C51135.07 (13)
C51—Ru1—C5—C68.28 (16)C48—Ru1—C50—C51104.16 (10)
Cl1—Ru1—C5—C697.36 (13)C53—Ru1—C50—C5165.71 (9)
C4—C5—C6—C70.39 (19)C52—Ru1—C50—C5129.85 (9)
Ru1—C5—C6—C7179.34 (11)Cl1—Ru1—C50—C5150.73 (9)
C4—C5—C6—C10175.82 (13)C1—Ru1—C50—C491.0 (2)
Ru1—C5—C6—C104.4 (2)C5—Ru1—C50—C4981.41 (9)
C5—C6—C7—C80.3 (2)C48—Ru1—C50—C4930.90 (9)
C10—C6—C7—C8176.21 (13)C53—Ru1—C50—C4969.36 (9)
C6—C7—C8—C90.2 (2)C52—Ru1—C50—C49105.22 (10)
C6—C7—C8—C18178.86 (13)C51—Ru1—C50—C49135.07 (13)
C5—C4—C9—C80.4 (2)Cl1—Ru1—C50—C49174.20 (7)
N1—C4—C9—C8178.58 (13)C49—C50—C51—C525.6 (2)
C7—C8—C9—C40.2 (2)Ru1—C50—C51—C5254.43 (13)
C18—C8—C9—C4178.87 (13)C49—C50—C51—C57172.49 (15)
C7—C6—C10—C1177.39 (17)Ru1—C50—C51—C57123.63 (16)
C5—C6—C10—C1199.03 (18)C49—C50—C51—Ru148.87 (13)
C7—C6—C10—C15101.14 (17)C1—Ru1—C51—C50148.47 (12)
C5—C6—C10—C1582.45 (18)C5—Ru1—C51—C5047.28 (11)
C15—C10—C11—C124.5 (2)C49—Ru1—C51—C5027.91 (9)
C6—C10—C11—C12176.97 (13)C48—Ru1—C51—C5065.56 (9)
C15—C10—C11—C16174.15 (14)C53—Ru1—C51—C50102.37 (10)
C6—C10—C11—C164.4 (2)C52—Ru1—C51—C50131.00 (14)
C10—C11—C12—C131.0 (2)Cl1—Ru1—C51—C50135.29 (8)
C16—C11—C12—C13177.74 (15)C1—Ru1—C51—C5217.47 (18)
C11—C12—C13—C142.8 (2)C5—Ru1—C51—C52178.28 (8)
C12—C13—C14—C153.0 (2)C49—Ru1—C51—C52103.09 (10)
C13—C14—C15—C100.5 (2)C48—Ru1—C51—C5265.44 (10)
C13—C14—C15—C17178.53 (16)C53—Ru1—C51—C5228.63 (9)
C11—C10—C15—C144.3 (2)C50—Ru1—C51—C52131.00 (14)
C6—C10—C15—C14177.23 (14)Cl1—Ru1—C51—C5293.71 (9)
C11—C10—C15—C17174.75 (15)C1—Ru1—C51—C5795.66 (19)
C6—C10—C15—C173.8 (2)C5—Ru1—C51—C5768.59 (17)
C7—C8—C18—C1986.40 (18)C49—Ru1—C51—C57143.79 (16)
C9—C8—C18—C1992.61 (17)C48—Ru1—C51—C57178.57 (16)
C7—C8—C18—C2394.86 (18)C53—Ru1—C51—C57141.76 (17)
C9—C8—C18—C2386.13 (17)C52—Ru1—C51—C57113.13 (19)
C23—C18—C19—C202.4 (2)C50—Ru1—C51—C57115.87 (19)
C8—C18—C19—C20176.33 (13)Cl1—Ru1—C51—C5719.42 (15)
C23—C18—C19—C24174.46 (13)C50—C51—C52—C530.2 (2)
C8—C18—C19—C246.8 (2)C57—C51—C52—C53177.94 (15)
C18—C19—C20—C211.3 (2)Ru1—C51—C52—C5354.62 (14)
C24—C19—C20—C21175.61 (14)C50—C51—C52—Ru154.77 (13)
C19—C20—C21—C220.3 (2)C57—C51—C52—Ru1123.32 (15)
C20—C21—C22—C230.7 (2)C1—Ru1—C52—C5356.44 (11)
C21—C22—C23—C180.4 (2)C5—Ru1—C52—C53127.03 (18)
C21—C22—C23—C25177.69 (14)C49—Ru1—C52—C5366.21 (10)
C19—C18—C23—C222.0 (2)C48—Ru1—C52—C5328.15 (9)
C8—C18—C23—C22176.77 (13)C50—Ru1—C52—C53102.99 (10)
C19—C18—C23—C25176.13 (14)C51—Ru1—C52—C53131.95 (14)
C8—C18—C23—C255.1 (2)Cl1—Ru1—C52—C53140.82 (9)
C1—N2—C26—C2746.2 (2)C1—Ru1—C52—C51171.62 (9)
C3—N2—C26—C27127.85 (16)C5—Ru1—C52—C514.9 (2)
C1—N2—C26—C31136.38 (15)C49—Ru1—C52—C5165.73 (9)
C3—N2—C26—C3149.5 (2)C48—Ru1—C52—C51103.79 (10)
C31—C26—C27—C280.6 (2)C53—Ru1—C52—C51131.94 (14)
N2—C26—C27—C28177.95 (14)C50—Ru1—C52—C5128.96 (9)
C26—C27—C28—C291.9 (2)Cl1—Ru1—C52—C5187.23 (9)
C26—C27—C28—C32178.81 (14)C51—C52—C53—C484.2 (2)
C27—C28—C29—C301.8 (2)Ru1—C52—C53—C4851.15 (13)
C32—C28—C29—C30178.88 (16)C51—C52—C53—Ru155.38 (14)
C28—C29—C30—C310.5 (3)C49—C48—C53—C523.0 (2)
C28—C29—C30—C40178.92 (16)C54—C48—C53—C52179.21 (15)
C29—C30—C31—C260.8 (2)Ru1—C48—C53—C5253.02 (14)
C40—C30—C31—C26179.79 (15)C49—C48—C53—Ru156.05 (12)
C27—C26—C31—C300.7 (2)C54—C48—C53—Ru1126.19 (14)
N2—C26—C31—C30176.63 (14)C1—Ru1—C53—C52132.84 (10)
C27—C28—C32—C37122.23 (17)C5—Ru1—C53—C52152.46 (12)
C29—C28—C32—C3758.5 (2)C49—Ru1—C53—C52102.99 (10)
C27—C28—C32—C3356.3 (2)C48—Ru1—C53—C52134.71 (14)
C29—C28—C32—C33122.98 (18)C50—Ru1—C53—C5264.81 (10)
C37—C32—C33—C341.4 (2)C51—Ru1—C53—C5229.22 (9)
C28—C32—C33—C34179.90 (16)Cl1—Ru1—C53—C5246.34 (10)
C37—C32—C33—C38178.61 (18)C1—Ru1—C53—C4892.45 (10)
C28—C32—C33—C380.1 (3)C5—Ru1—C53—C4817.75 (17)
C32—C33—C34—C350.1 (3)C49—Ru1—C53—C4831.71 (9)
C38—C33—C34—C35179.9 (2)C52—Ru1—C53—C48134.71 (14)
C33—C34—C35—C361.1 (3)C50—Ru1—C53—C4869.90 (9)
C34—C35—C36—C370.9 (3)C51—Ru1—C53—C48105.49 (10)
C33—C32—C37—C361.5 (2)Cl1—Ru1—C53—C48178.95 (8)
C28—C32—C37—C36179.97 (14)C49—C48—C54—C5631.6 (2)
C33—C32—C37—C39176.19 (16)C53—C48—C54—C56150.78 (15)
C28—C32—C37—C392.3 (2)Ru1—C48—C54—C5658.6 (2)
C35—C36—C37—C320.4 (3)C49—C48—C54—C5592.70 (18)
C35—C36—C37—C39177.39 (18)C53—C48—C54—C5584.92 (19)
C29—C30—C40—C4199.8 (2)Ru1—C48—C54—C55177.14 (12)
C31—C30—C40—C4180.8 (2)C63—C58—C59—C600.2 (3)
C29—C30—C40—C4585.0 (2)C58—C59—C60—C610.2 (3)
C31—C30—C40—C4594.5 (2)C59—C60—C61—C620.4 (3)
C45—C40—C41—C421.6 (3)C60—C61—C62—C630.5 (3)
C30—C40—C41—C42176.67 (16)C61—C62—C63—C580.5 (3)
C45—C40—C41—C46177.65 (18)C59—C58—C63—C620.3 (3)
C30—C40—C41—C462.5 (3)C69—C64—C65—C660.5 (4)
C40—C41—C42—C432.0 (3)C64—C65—C66—C670.4 (4)
C46—C41—C42—C43177.2 (2)C65—C66—C67—C680.2 (3)
C41—C42—C43—C440.6 (3)C66—C67—C68—C690.5 (3)
C42—C43—C44—C451.2 (3)C67—C68—C69—C640.3 (4)
C43—C44—C45—C401.6 (3)C65—C64—C69—C680.2 (4)
C43—C44—C45—C47179.9 (2)

Experimental details

Crystal data
Chemical formula[Ru(C47H43N2)Cl(C10H14)]·2C6H6
Mr1062.78
Crystal system, space groupMonoclinic, P21/a
Temperature (K)123
a, b, c (Å)12.9207 (12), 19.2867 (17), 22.977 (2)
β (°) 98.6792 (18)
V3)5660.3 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.20 × 0.19 × 0.11
Data collection
DiffractometerRigaku Saturn CCD
diffractometer
Absorption correctionMulti-scan
(REQAB; Jacobson, 1998)
Tmin, Tmax0.930, 0.961
No. of measured, independent and
observed [I > 2σ(I)] reflections
22748, 12805, 10644
Rint0.016
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.092, 1.09
No. of reflections12805
No. of parameters669
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.55, 0.95

Computer programs: CrystalClear (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Yadokari-XG 2009 (Kabuto et al., 2009).

 

Acknowledgements

This work was partly supported by Grants-in-Aid for The Global COE Program for Education and Research Center for Emergence of New Mol­ecular Chemistry and for Scientific Research on Innovative Areas `Mol­ecular Activation Directed toward Straightforward Synthesis' from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

References

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First citationJacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.  Google Scholar
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First citationZhang, C. Y., Zhao, Y., Li, B., Song, H. B., Xu, S. S. & Wang, B. Q. (2009). Dalton Trans. pp. 5182–5189.  Web of Science CSD CrossRef Google Scholar

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