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Volume 68 
Part 1 
Page o64  
January 2012  

Received 11 November 2011
Accepted 2 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.148
Data-to-parameter ratio = 15.3
Details
Open access

(E)-2-(4-tert-Butylphenyl)-2-cyano-1-(3-methyl-1-vinyl-1H-pyrazol-5-yl)vinyl 2,2-dimethylpropanoate

aShenyang University of Chemical Technology, Shenyang 110142, People's Republic of China, and bAgrochemicals Division, Shenyang Research Institute of Chemical Industry, Shenyang 110021, People's Republic of China
Correspondence e-mail: yangguiqiu@gmail.com

In the title compound, C24H29N3O2, the dihedral angle between the benzene and pyrazole rings is 80.55 (7)°. The molecule contains an acrylonitrile moiety and exists in an E conformation. Bioassay tests showed that the title compound exhibited higher acaricidal activity than its Z isomer.

Related literature

For background to acrylonitrile compounds, see: Boedec et al. (2008[Boedec, A., Sicard, H., Dessolin, J., Herbette, G., Ingoure, S., Raymond, C., Belmant, C. & Kraus, J. L. (2008). J. Med. Chem. 51, 1747-1754.]); Napolitano et al. (2001[Napolitano, A., Bruno, I., Rovero, P., Lucas, R., Peris, M. P. & Riccio, R. (2001). Tetrahedron, 57, 6249-6255.]); Reggio et al. (1998[Reggio, P. H., Basu, S., Barnett, J., Castro, M. T., Hurst, D. P., Seltzman, H. H., Roche, M. J., Gilliam, A. F., Thomas, B. F. & Stevenson, L. A. (1998). J. Med. Chem. 41, 5177-5187.]). For further synthetic details, see: Kenzo et al. (2006[Kenzo, F., Yasuo, K., Norio, T., Hideaki, S., Masatoshi, O. & Koichi, N. (2006). US Patent 20060178523.]); Yang et al. (2009[Yang, P., Shen, D. L., Tan, C. X., Weng, J. Q., Lu, Q., Wei, Y. C. & Kong, X. L. (2009). Zhe. Daxue Xuebao, 36, 183-185.]).

[Scheme 1]

Experimental

Crystal data
  • C24H29N3O2

  • Mr = 391.50

  • Orthorhombic, P b c a

  • a = 12.0056 (16) Å

  • b = 19.283 (3) Å

  • c = 20.183 (3) Å

  • V = 4672.5 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.38 × 0.36 × 0.32 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.978

  • 22480 measured reflections

  • 4118 independent reflections

  • 2871 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.148

  • S = 1.05

  • 4118 reflections

  • 269 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: HB6506 ).


References

Boedec, A., Sicard, H., Dessolin, J., Herbette, G., Ingoure, S., Raymond, C., Belmant, C. & Kraus, J. L. (2008). J. Med. Chem. 51, 1747-1754.  [ISI] [PubMed] [ChemPort]
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kenzo, F., Yasuo, K., Norio, T., Hideaki, S., Masatoshi, O. & Koichi, N. (2006). US Patent 20060178523.
Napolitano, A., Bruno, I., Rovero, P., Lucas, R., Peris, M. P. & Riccio, R. (2001). Tetrahedron, 57, 6249-6255.  [ISI] [CrossRef] [ChemPort]
Reggio, P. H., Basu, S., Barnett, J., Castro, M. T., Hurst, D. P., Seltzman, H. H., Roche, M. J., Gilliam, A. F., Thomas, B. F. & Stevenson, L. A. (1998). J. Med. Chem. 41, 5177-5187.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yang, P., Shen, D. L., Tan, C. X., Weng, J. Q., Lu, Q., Wei, Y. C. & Kong, X. L. (2009). Zhe. Daxue Xuebao, 36, 183-185.  [ChemPort]


Acta Cryst (2012). E68, o64  [ doi:10.1107/S1600536811052007 ]

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