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Volume 65 
Part 3 
Pages m243-m244  
March 2009  

Received 26 January 2009
Accepted 28 January 2009
Online 4 February 2009

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Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.006 Å
R = 0.049
wR = 0.115
Data-to-parameter ratio = 15.1
Details
Open access

Dichlorido[1-(2-methylbenzyl)-3-([eta]6-2,4,6-trimethylbenzyl)-1H-2,3-dihydrobenzimidazol-2-ylidene]ruthenium(II) dichloromethane solvate

Hakan Arslan,a,b* Don VanDerveer,c Sedat Yasar,d Ismail Özdemird and Bekir Çetinkayae

aDepartment of Natural Sciences, Fayetteville State University, NC 28301, USA,bDepartment of Chemistry, Faculty of Pharmacy, Mersin University, Mersin TR 33169, Turkey,cDepartment of Chemistry, Clemson University, SC 29634, USA,dDepartment of Chemistry, Faculty of Sciences and Arts, Inönü University, Malatya TR 44280, Turkey, and eDepartment of Chemistry, Faculty of Science, Ege University, Bornova-Izmir TR 35100, Turkey
Correspondence e-mail: hakan.arslan.acad@gmail.com

The title complex, [RuCl2(C25H26N2)]·CH2Cl2, is best thought of as containing an octahedrally coordinated Ru center with the arene occupying three sites. Two Ru-Cl bonds and one Ru-carbene bond complete the distorted octahedron. The carbene portion of the ligand is a benzimidazole ring. This ring is connected to the C6H2(CH3)3 arene group by a CH2 bridge. This leads to a system with very little apparent strain. A dichloromethane solvent molecule completes the crystal structure. Further stabilization is accomplished via C-H...N and C-H...Cl interactions.

Related literature

For synthesis, see: Yasar et al. (2008[Yasar, S., Özdemir, I., Çetinkaya, B., Renaud, J. L. & Bruneau, C. (2008). Eur. J. Org. Chem. 12, 2142-2149.]); Çetinkaya et al. (2001[Çetinkaya, B., Demir, S., Özdemir, I., Toupet, L., Semeril, D., Bruneau, C. & Dixneuf, P. H. (2001). New J. Chem. 25, 519-521.], 2003[Çetinkaya, B., Demir, S., Özdemir, I., Toupet, L., Semeril, D., Bruneau, C. & Dixneuf, P. H. (2003). Chem. Eur. J. 9, 2323-2330.]); Özdemir et al. (2001[Özdemir, I., Yigit, B., Çetinkaya, B., Ülkü, D., Tahir, M. N. & Arici, C. (2001). J. Organomet. Chem. 633, 27-32.], 2004[Özdemir, I., Alici, B., Gürbüz, N., Çetinkaya, E. & Çetinkaya, B. (2004). J. Mol. Catal. A Chem. 217, 37-40.]). For general background, see: Herrmann (2002[Herrmann, W. A. (2002). Angew. Chem. Int. Ed. 41, 1290-1309.]); Herrmann et al. (1995[Herrmann, W. A., Elison, M., Fischer, J., Köcher, C. & Artus, G. R. J. (1995). Angew. Chem. Int. Ed. Engl. 34, 2371-2374.]); Navarro et al. (2006[Navarro, O., Marion, N., Oonishi, Y., Kelly, R. A. & Nolan, S. P. (2006). J. Org. Chem. 71, 685-692.]); Arduengo & Krafczyc (1998[Arduengo, A. J. & Krafczyc, R. (1998). Chem. Ztg, 32, 6-14.]). For related compounds, see: Begley et al. (1991[Begley, M. J., Harrison, S. & Wright, A. H. (1991). Acta Cryst. C47, 318-320.]); Steedman & Burrell (1997[Steedman, A. J. & Burrell, A. K. (1997). Acta Cryst. C53, 864-866.]); Arslan et al. (2004[Arslan, H., VanDerveer, D., Özdemir, I., Çetinkaya, B. & Demir, S. (2004). Z. Kristallogr. New Cryst. Struct. 219, 377-378.], 2005[Arslan, H., VanDerveer, D., Özdemir, I., Yasar, S. & Çetinkaya, B. (2005). Acta Cryst. E61, m1873-m1875.], 2007[Arslan, H., VanDerveer, D., Yasar, S., Özdemir, I. & Çetinkaya, B. (2007). Acta Cryst. E63, m1001-m1003.]).

[Scheme 1]

Experimental

Crystal data

  • [RuCl2(C25H26N2)]·CH2Cl2

  • Mr = 611.37

  • Monoclinic, C 2/c

  • a = 31.362 (6) Å

  • b = 8.1014 (16) Å

  • c = 20.484 (4) Å

  • [beta] = 100.11 (3)°

  • V = 5123.8 (18) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 1.05 mm-1

  • T = 153 (2) K

  • 0.46 × 0.14 × 0.06 mm
Data collection

  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998[Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.]) Tmin = 0.644, Tmax = 0.940

  • 15807 measured reflections

  • 4501 independent reflections

  • 3825 reflections with I > 2[sigma](I)

  • Rint = 0.054
Refinement

  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.115

  • S = 1.08

  • 4501 reflections

  • 298 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.92 e Å-3

  • [Delta][rho]min = -0.73 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15C...N2 0.98 2.60 3.244 (7) 123
C18-H18A...Cl2 0.99 2.67 3.468 (5) 138
C23-H23A...Cl1i 0.95 2.78 3.730 (5) 175
C26-H26A...Cl2ii 0.99 2.46 3.431 (6) 168
Symmetry codes: (i) [x, -y, z-{\script{1\over 2}}]; (ii) x, y+1, z.

Data collection: CrystalClear (Rigaku/MSC, 2006[Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2716 ).

Acknowledgements

We thank the Technological and Scientific Research Council of Turkey TÜBITAK-CNRS [grant No. TBAG-U/181(106 T716)] and Inönü University Research Fund (BAP 2007/39) for financial support.

References

Arduengo, A. J. & Krafczyc, R. (1998). Chem. Ztg, 32, 6-14.  [ChemPort]
Arslan, H., VanDerveer, D., Özdemir, I., Çetinkaya, B. & Demir, S. (2004). Z. Kristallogr. New Cryst. Struct. 219, 377-378.  [ChemPort]
Arslan, H., VanDerveer, D., Özdemir, I., Yasar, S. & Çetinkaya, B. (2005). Acta Cryst. E61, m1873-m1875.  [CrossRef] [details]
Arslan, H., VanDerveer, D., Yasar, S., Özdemir, I. & Çetinkaya, B. (2007). Acta Cryst. E63, m1001-m1003.  [CSD] [CrossRef] [details]
Begley, M. J., Harrison, S. & Wright, A. H. (1991). Acta Cryst. C47, 318-320.  [CrossRef] [details]
Çetinkaya, B., Demir, S., Özdemir, I., Toupet, L., Semeril, D., Bruneau, C. & Dixneuf, P. H. (2001). New J. Chem. 25, 519-521.
Çetinkaya, B., Demir, S., Özdemir, I., Toupet, L., Semeril, D., Bruneau, C. & Dixneuf, P. H. (2003). Chem. Eur. J. 9, 2323-2330.
Herrmann, W. A. (2002). Angew. Chem. Int. Ed. 41, 1290-1309.  [ISI] [CrossRef] [ChemPort]
Herrmann, W. A., Elison, M., Fischer, J., Köcher, C. & Artus, G. R. J. (1995). Angew. Chem. Int. Ed. Engl. 34, 2371-2374.  [CrossRef] [ChemPort] [ISI]
Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.
Navarro, O., Marion, N., Oonishi, Y., Kelly, R. A. & Nolan, S. P. (2006). J. Org. Chem. 71, 685-692.  [CrossRef] [PubMed] [ChemPort]
Özdemir, I., Alici, B., Gürbüz, N., Çetinkaya, E. & Çetinkaya, B. (2004). J. Mol. Catal. A Chem. 217, 37-40.  [CrossRef]
Özdemir, I., Yigit, B., Çetinkaya, B., Ülkü, D., Tahir, M. N. & Arici, C. (2001). J. Organomet. Chem. 633, 27-32.  [CrossRef]
Rigaku/MSC (2006). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Steedman, A. J. & Burrell, A. K. (1997). Acta Cryst. C53, 864-866.  [CrossRef] [details]
Yasar, S., Özdemir, I., Çetinkaya, B., Renaud, J. L. & Bruneau, C. (2008). Eur. J. Org. Chem. 12, 2142-2149.

Acta Cryst (2009). E65, m243-m244   [ doi:10.1107/S160053680900350X ]

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