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Volume 69 
Part 3 
Pages o326-o327  
March 2013  

Received 20 December 2012
Accepted 14 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.044
wR = 0.107
Data-to-parameter ratio = 11.5
Details
Open access

2-{(E)-4-[4-(Trifluoromethyl)phenoxy]but-2-enyloxy}phenyl N-methylcarbamate

aCollege of Plant Science & Technology of Huazhong Agricultural University, Wuhan 430070, People's Republic of China, and bKey Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, People's Republic of China
Correspondence e-mail: jning502@yahoo.com.cn

In the title compound, C19H18F3NO4, which was designed and synthesized as a dual-site inhibitor of insect AChE (acetylcholinesterase), the dihedral angle between the methylcarbamate group and the benzene ring is 72.47 (6)°. In the crystal, inversion dimers are linked by pairs of N-H...O hydrogen bonds.

Related literature

For background to multivalent ligand-receptor interactions and their pharmaceutical applications, see: Carlier et al. (1999[Carlier, P. R., Chow, E. S. H., Han, Y., Liu, J., Yazal, J. E. & Pang, Y. R. (1999). J. Med. Chem. 42, 4225-4231.]); Hu et al. (2002[Hu, M. K., Wu, L. J., Hsiao, G. & Yen, M. H. (2002). J. Med. Chem. 45, 2277-2282.]); Kitov et al. (2000[Kitov, P. I., Sadowska, J. M., Mulvey, G., Armstrong, G. D., Ling, H., Pannu, N. S., Read, R. J. & Bundle, D. R. (2000). Nature, 403, 669-672.]); Kopytek et al. (2000[Kopytek, S. J., Standaert, R. F., Dyer, J. C. D. & Hu, J. C. (2000). Chem. Biol. 7, 313-321.]); Kryger et al. (1999[Kryger, G., Silman, I. & Sussman, J. (1999). Structure, 7, 297-306.]); Lee & Lee (1995[Lee, Y. C. & Lee, R. T. (1995). Acc. Chem. Res. 28, 321-327.]); Luedtke et al. (2003[Luedtke, N. W., Lui, Q. & Tor, Y. (2003). Biochemistry, 42, 11391-11403.]); Mammen et al. (1998[Mammen, M., Choi, S. K. & Whitesides, G. M. (1998). Angew. Chem. Int. Ed. 37, 2754-2794.]); Pang et al. (1996[Pang, Y. P., Quiram, P., Jelacic, T., Hong, F. & Brimijoin, S. (1996). J. Biol. Chem. 271, 23646-23649.]). For agrochemical applications of the cluster effect, see: Ma et al. (2010[Ma, H. J., Xie, R. L., Zhao, Q. F., Mei, X. D. & Ning, J. (2010). J. Agric. Food Chem. 58, 12817-12821.]); Zhao et al. (2008[Zhao, Q. F., Yang, G. Q., Mei, X. D., Yuan, H. Z. & Ning, J. (2008). J. Pestic. Sci. 33, 371-375.], 2009[Zhao, Q. F., Yang, G. Q., Mei, X. D., Yuan, H. Z. & Ning, J. (2009). Pestic. Biochem. Physiol. 95, 131-134.]). For the structure of AChE from Torpedo californica (TcAChe), see: Sussman et al. (1991[Sussman, J. L., Harel, M., Frolow, F., Oefner, C., Goldman, A., Toker, L. & Silman, I. (1991). Science, 253, 872-879.]); Harel et al. (1993[Harel, M., Schalk, I., Ehret-Sabatier, L., Bouet, F., Goeldner, M., Hirth, C., Axelsen, P. H., Silman, I. & Sussman, J. L. (1993). Proc. Natl. Acad. Sci. USA, 90, 9031-9035.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18F3NO4

  • Mr = 381.34

  • Monoclinic, P 21 /c

  • a = 12.413 (3) Å

  • b = 9.3936 (19) Å

  • c = 16.202 (3) Å

  • [beta] = 111.65 (3)°

  • V = 1755.9 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.05 mm-1

  • T = 173 K

  • 0.47 × 0.30 × 0.25 mm

Data collection
  • Rigaku R-AXIS RAPID IP area-detector diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.639, Tmax = 0.780

  • 11613 measured reflections

  • 3163 independent reflections

  • 2615 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.107

  • S = 1.07

  • 3163 reflections

  • 274 parameters

  • 60 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.88 2.22 3.072 (2) 163
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku 2001[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2102 ).


Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (program No. 31201554), the China Postdoctoral Science Foundation (program No. 20110491174) and the Fundamental Research Funds for the Central Universities (program No. 2011QC086).

References

Carlier, P. R., Chow, E. S. H., Han, Y., Liu, J., Yazal, J. E. & Pang, Y. R. (1999). J. Med. Chem. 42, 4225-4231.  [ISI] [CrossRef] [PubMed] [ChemPort]
Harel, M., Schalk, I., Ehret-Sabatier, L., Bouet, F., Goeldner, M., Hirth, C., Axelsen, P. H., Silman, I. & Sussman, J. L. (1993). Proc. Natl. Acad. Sci. USA, 90, 9031-9035.  [CrossRef] [ChemPort] [PubMed]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Hu, M. K., Wu, L. J., Hsiao, G. & Yen, M. H. (2002). J. Med. Chem. 45, 2277-2282.  [ISI] [CrossRef] [PubMed]
Kitov, P. I., Sadowska, J. M., Mulvey, G., Armstrong, G. D., Ling, H., Pannu, N. S., Read, R. J. & Bundle, D. R. (2000). Nature, 403, 669-672.  [ISI] [PubMed] [ChemPort]
Kopytek, S. J., Standaert, R. F., Dyer, J. C. D. & Hu, J. C. (2000). Chem. Biol. 7, 313-321.  [CrossRef] [PubMed] [ChemPort]
Kryger, G., Silman, I. & Sussman, J. (1999). Structure, 7, 297-306.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lee, Y. C. & Lee, R. T. (1995). Acc. Chem. Res. 28, 321-327.  [CrossRef] [ChemPort] [ISI]
Luedtke, N. W., Lui, Q. & Tor, Y. (2003). Biochemistry, 42, 11391-11403.  [ISI] [CrossRef] [PubMed] [ChemPort]
Ma, H. J., Xie, R. L., Zhao, Q. F., Mei, X. D. & Ning, J. (2010). J. Agric. Food Chem. 58, 12817-12821.  [ISI] [CrossRef] [ChemPort] [PubMed]
Mammen, M., Choi, S. K. & Whitesides, G. M. (1998). Angew. Chem. Int. Ed. 37, 2754-2794.  [CrossRef]
Pang, Y. P., Quiram, P., Jelacic, T., Hong, F. & Brimijoin, S. (1996). J. Biol. Chem. 271, 23646-23649.  [ChemPort] [PubMed]
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sussman, J. L., Harel, M., Frolow, F., Oefner, C., Goldman, A., Toker, L. & Silman, I. (1991). Science, 253, 872-879.  [CrossRef] [PubMed] [ChemPort] [ISI]
Zhao, Q. F., Yang, G. Q., Mei, X. D., Yuan, H. Z. & Ning, J. (2008). J. Pestic. Sci. 33, 371-375.  [CrossRef] [ChemPort]
Zhao, Q. F., Yang, G. Q., Mei, X. D., Yuan, H. Z. & Ning, J. (2009). Pestic. Biochem. Physiol. 95, 131-134.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o326-o327   [ doi:10.1107/S1600536813001347 ]

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