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Volume 65 
Part 1 
Pages m97-m98  
January 2009  

Received 24 November 2008
Accepted 11 December 2008
Online 20 December 2008

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.016 Å
Disorder in main residue
R = 0.089
wR = 0.255
Data-to-parameter ratio = 14.5
Details
Open access

Bromido[1-([eta]6-4-tert-butylbenzyl)-3-(2,4,6-trimethylbenzyl)benzimidazol-2-ylidene]chloridoruthenium(II)

aDepartment of Natural Sciences, Fayetteville State University, Fayetteville, NC 28301, USA,bDepartment of Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR 33169, Turkey,cDepartment of Chemistry, Clemson University, Clemson, SC 29634, USA,dDepartment of Chemistry, Faculty of Science 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

A new ruthenium complex, [RuBrCl(C28H32N2)], has been synthesized and characterized by elemental analysis, 1H NMR, 13C NMR, IR-spectroscopy and a single-crystal X-ray diffraction study. The Ru atom in this complex is best described as having a considerably distorted octahedral coordination environment with the arene occupying three coordination sites. Two further coordination sites are occupied by chloride and bromide ligands, while the sixth site is occupied by the carbene. The carbene portion of the ligand is a benzimidazole ring. This ring is connected to the C6H4C(CH3)3 arene by a CH2 bridge. This leads to a system with very little apparent strain. The two halogen atoms are disordered between Br and Cl. Two partial Cl atoms share the same sites as two partial Br atoms so that the title compound effectively has one Cl and one Br atom. C-H...X (X = Cl, Br) hydrogen bonds help to stabilize the crystal structure.

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. (2003[Çetinkaya, B., Demir, S., Özdemir, I., Toupet, L., Semeril, D., Bruneau, C. & Dixneuf, P. H. (2003). Chem. Eur. J. 9, 2323-2330.]). For general background, see: Herrmann (2002[Herrmann, W. A. (2002). Angew. Chem. Int. Ed. 41, 1290-1309.]); Arduengo & Krafczyc (1998[Arduengo, A. J. & Krafczyc, R. (1998). Chem. Ztg. 32, 6-14.]); Arduengo et al. (1991[Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.]). For related compounds, see: Begley et al. (1991[Begley, M. J., Harrison, S. & Wright, A. H. (1991). Acta Cryst. C47, 318-320.]); Arslan et al. (2004b[Arslan, H., VanDerveer, D., Özdemir, I., Çetinkaya, B. & Demir, S. (2004b). Z. Kristallogr. New Cryst. Struct. 219, 377-378.], 2005a[Arslan, H., VanDerveer, D., Özdemir, I., Çetinkaya, B. & Demir, S. (2005a). J. Chem. Crystallogr. 35, 491-495.],b[Arslan, H., VanDerveer, D., Özdemir, I., Yasar, S. & Çetinkaya, B. (2005b). Acta Cryst. E61, m1873-m1875.], 2007b[Arslan, H., VanDerveer, D., Yasar, S., Özdemir, I. & Çetinkaya, B. (2007b). Acta Cryst. E63, m942-m944.],c[Arslan, H., VanDerveer, D., Yasar, S., Özdemir, I. & Çetinkaya, B. (2007c). Acta Cryst. E63, m1001-m1003.]). For related literature, see: Arslan et al. (2004a[Arslan, H., VanDerveer, D., Özdemir, I., Çetinkaya, B. & Yasar, S. (2004a). Z. Kristallogr. New Cryst. Struct. 219, 44-46.], 2007a[Arslan, H., VanDerveer, D., Özdemir, I., Demir, S. & Çetinkaya, B. (2007a). Acta Cryst. E63, m770-m771.]); 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.]); Özdemir et al. (2001[Özdemir, I., Yigit, B., Çetinkaya, B., Ülkü, D., Tahir, M. N. & Arici, C. (2001). J. Organomet. Chem. 633, 27-32.]); 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.], 2002[Çetinkaya, B., Seckin, T., Gürbüz, N. & Özdemir, I. (2002). J. Mol. Catal. A, 184, 31-38.]).

[Scheme 1]

Experimental

Crystal data
  • [RuBrCl(C28H32N2)]

  • Mr = 611.69

  • Monoclinic, P 21 /n

  • a = 7.6336 (15) Å

  • b = 27.725 (6) Å

  • c = 12.051 (2) Å

  • [beta] = 98.80 (3)°

  • V = 2520.5 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.29 mm-1

  • T = 153 (2) K

  • 0.26 × 0.12 × 0.02 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 = 0.581, Tmax = 0.955

  • 17799 measured reflections

  • 4449 independent reflections

  • 3288 reflections with I > 2[sigma](I)

  • Rint = 0.089

Refinement
  • R[F2 > 2[sigma](F2)] = 0.089

  • wR(F2) = 0.255

  • S = 1.04

  • 4449 reflections

  • 306 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 2.45 e Å-3

  • [Delta][rho]min = -1.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14-H14...Cl2i 0.96 2.65 3.406 (11) 135
C16-H16C...Br1 0.96 2.92 3.563 (11) 125
C19-H19A...Br1 0.96 2.92 3.323 (11) 106
Symmetry code: (i) x+1, y, 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: AT2686 ).


Acknowledgements

We thank the Scientific and Technological Research Council of Turkey TÜBITAK-CNRS [TBAG-U/181 (106 T716)] and Inönü University Research Fund (BAP. 2008/03 Güdümlü) for financial support.

References

Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361-363.  [CrossRef] [ChemPort] [ISI]
Arduengo, A. J. & Krafczyc, R. (1998). Chem. Ztg. 32, 6-14.  [ChemPort]
Arslan, H., VanDerveer, D., Özdemir, I., Çetinkaya, B. & Demir, S. (2004b). Z. Kristallogr. New Cryst. Struct. 219, 377-378.  [ChemPort]
Arslan, H., VanDerveer, D., Özdemir, I., Çetinkaya, B. & Demir, S. (2005a). J. Chem. Crystallogr. 35, 491-495.  [ISI] [CSD] [CrossRef] [ChemPort]
Arslan, H., VanDerveer, D., Özdemir, I., Çetinkaya, B. & Yasar, S. (2004a). Z. Kristallogr. New Cryst. Struct. 219, 44-46.  [ChemPort]
Arslan, H., VanDerveer, D., Özdemir, I., Demir, S. & Çetinkaya, B. (2007a). Acta Cryst. E63, m770-m771.  [CSD] [CrossRef] [details]
Arslan, H., VanDerveer, D., Özdemir, I., Yasar, S. & Çetinkaya, B. (2005b). Acta Cryst. E61, m1873-m1875.  [CSD] [CrossRef] [details]
Arslan, H., VanDerveer, D., Yasar, S., Özdemir, I. & Çetinkaya, B. (2007b). Acta Cryst. E63, m942-m944.  [CSD] [CrossRef] [details]
Arslan, H., VanDerveer, D., Yasar, S., Özdemir, I. & Çetinkaya, B. (2007c). 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.
Çetinkaya, B., Seckin, T., Gürbüz, N. & Özdemir, I. (2002). J. Mol. Catal. A, 184, 31-38.  [CrossRef]
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., Yigit, B., Çetinkaya, B., Ülkü, D., Tahir, M. N. & Arici, C. (2001). J. Organomet. Chem. 633, 27-32.
Rigaku/MSC (2006). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [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, m97-m98   [ doi:10.1107/S1600536808042256 ]

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