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

Yang, G.; Wang, Y.; Yu, H.

doi:10.1107/S1600536811052007

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 (C-C) = 0.003 Å
R = 0.048
wR = 0.148
Data-to-parameter ratio = 15.3
Details

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

Guiqiu Yang,^a ^* Yang Wang ^a and Haibo Yu ^b

^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); Napolitano et al. (2001); Reggio et al. (1998). For further synthetic details, see: Kenzo et al. (2006); Yang et al. (2009).

Experimental

Crystal data

C₂₄H₂₉N₃O₂
M_r = 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 radiation
= 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) T_min = 0.973, T_max = 0.978
22480 measured reflections
4118 independent reflections
2871 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.148
S = 1.05
4118 reflections
269 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.20 e Å^-3

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.

organic compounds