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Volume 64 
Part 6 
Page o972  
June 2008  

Received 31 March 2008
Accepted 19 April 2008
Online 3 May 2008

[bx2137sup1]
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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.141
Data-to-parameter ratio = 16.2
Details
Open access

2-Methyl-5-nitrobenzonitrile

Wen-Xian Lianga and Guo-Xi Wanga*

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: fudavid88@yahoo.com.cn

In the title compound, C8H6N2O2, the nitro group is rotated by 10.2 (2)° out of the plane of the benzene ring. The crystal structure is stabilized by van der Waals interactions.

Related literature

For the chemistry of nitrile derivatives, see: Xiong et al. (2002[Xiong, R.-G., Xue, X., Zhao, H., You, X.-Z., Abrahams, B. F. & Xue, Z.-L. (2002). Angew. Chem. Int. Ed. 41, 3800-3803.]); Jin et al. (1994[Jin, Z., Nolan, K., McArthur, C. R., Lever, A. B. P. & Leznoff, C. C. (1994). J. Organomet. Chem. 468, 205-212.]); Brewis et al. (2003[Brewis, M., Helliwell, M. & McKeown, N. B. (2003). Tetrahedron, 59, 3863-3872.]); Dunica et al. (1991[Dunica, J. V., Pierce, M. E. & Santella, J. B. (1991). J. Org. Chem. 56, 2395-2400.]). For related literature, see: Fu & Zhao (2007[Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.]).

[Scheme 1]

Experimental

Crystal data

  • C8H6N2O2

  • Mr = 162.15

  • Monoclinic, P 21 /n

  • a = 3.8946 (8) Å

  • b = 7.6350 (15) Å

  • c = 26.180 (5) Å

  • [beta] = 91.65 (3)°

  • V = 778.1 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 (2) K

  • 0.4 × 0.35 × 0.2 mm
Data collection

  • Rigaku Mercury2 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.93, Tmax = 0.98

  • 7390 measured reflections

  • 1761 independent reflections

  • 1273 reflections with I > 2[sigma](I)

  • Rint = 0.038
Refinement

  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.141

  • S = 1.04

  • 1761 reflections

  • 109 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2137 ).

Acknowledgements

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong.

References

Brewis, M., Helliwell, M. & McKeown, N. B. (2003). Tetrahedron, 59, 3863-3872.  [ISI] [CSD] [CrossRef] [ChemPort]
Dunica, J. V., Pierce, M. E. & Santella, J. B. (1991). J. Org. Chem. 56, 2395-2400.
Fu, D.-W. & Zhao, H. (2007). Acta Cryst. E63, o3206.  [CSD] [CrossRef] [details]
Jin, Z., Nolan, K., McArthur, C. R., Lever, A. B. P. & Leznoff, C. C. (1994). J. Organomet. Chem. 468, 205-212.  [CrossRef] [ChemPort]
Rigaku/MSC (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Xiong, R.-G., Xue, X., Zhao, H., You, X.-Z., Abrahams, B. F. & Xue, Z.-L. (2002). Angew. Chem. Int. Ed. 41, 3800-3803.  [CrossRef] [ChemPort]

Acta Cryst (2008). E64, o972  [ doi:10.1107/S1600536808010982 ]

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