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Volume 69 
Part 7 
Pages o1064-o1065  
July 2013  

Received 9 May 2013
Accepted 23 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.041
wR = 0.134
Data-to-parameter ratio = 15.6
Details
Open access

3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl 3-(2-bromo-4-fluorophenyl)acrylate

aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China, and bMinistry of Agriculture Key Laboratory of Agricultural Entomology, Institute of Pesticide and Environmental Toxicology, Zhejiang University, Hangzhou 310029, People's Republic of China
Correspondence e-mail: jinhaozhao@zju.edu.cn

In the title compound, C27H27BrFNO4, which is an inhibitor of acetyl-CoA carboxylase, the cyclohexane ring displays a chair comformation with the spiro-C and methoxy-bearing C atoms deviating by 0.681 (7) and -0.655 (1) Å, resppectively, from the mean plane formed by the other four C atoms of the spiro-C6 ring. The mean planes of the cyclohexane and 2-bromo-4-fluorophenyl rings are nearly perpendicular to that of the pyrrolidine ring, making dihedral angles 89.75 (6) and 87.60 (9)°, respectively. In the crystal, molecules are linked via pairs of N-H...O hydrogen bonds, forming inversion dimers.

Related literature

For the pesticide spirotetramat (systematic name: cis-3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate), the central unit of the title compound, see: Fischer & Weiss (2008[Fischer, R. & Weiss, H. C. (2008). Bayer CropSci. J. 61, 127-140.]); Maus (2008[Maus, C. (2008). Bayer CropSci. J. 61, 159-180.]). For structures of spirotetramat derivatives, see: Fischer et al. (2010[Fischer, R., Bretschneider, T., Lehr, S., Arnold, C., Dittgen, J., Feucht, D., Kehne, H., Malsam, O., Rosinger, C. H., Franken, E. M. & Goergens, U. (2010). US Patent No. 20100279873A1.]); Campbell et al. (1985[Campbell, A. C., Maidment, M. S., Pick, J. H. & Stevenson, D. F. M. (1985). J. Chem. Soc. Perkin Trans. 1, pp. 1567-1576.]); Schobert & Schlenk (2008[Schobert, R. & Schlenk, A. (2008). Bioorg. Med. Chem. 16, 4203-4221.]); Zhao et al. (2012[Zhao, J. H., Zhang, J. G., Xu, B. R., Wang, Z. C., Cheng, J. L. & Zhu, G. N. (2012). J. Agric. Food Chem. 60, 4779-4787.]); Wang et al. (2011[Wang, Z. C., Xu, B. R. & Cheng, J. L. (2011). Chin. J. Struc. Chem. 30, 1675-1679.]). For the metabolic transformation of spirotetramat, see: Bruck et al. (2009[Bruck, E., Elbert, A., Fischer, R. & Krueger, S. (2009). Crop Prot. 28, 838-844.]).

[Scheme 1]

Experimental

Crystal data
  • C27H27BrFNO4

  • Mr = 528.41

  • Triclinic, [P \overline 1]

  • a = 10.5170 (5) Å

  • b = 11.2410 (6) Å

  • c = 12.5150 (7) Å

  • [alpha] = 110.364 (2)°

  • [beta] = 102.049 (2)°

  • [gamma] = 107.409 (1)°

  • V = 1239.95 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.70 mm-1

  • T = 296 K

  • 0.48 × 0.45 × 0.24 mm

Data collection
  • Rigaku R-AXIS RAPID/ZJUG diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.446, Tmax = 0.665

  • 10805 measured reflections

  • 4845 independent reflections

  • 3433 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.134

  • S = 1.00

  • 4845 reflections

  • 311 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.95 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.11 2.859 (4) 145
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: PROCESS-AUTO (Rigaku, 2006[Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2194 ).


Acknowledgements

This project was supported by the National Natural Science Foundation of China (No. 31101470) and the Fundamental Research Funds for Universities - Educational Commission of Zhejiang Province (No. Y201224393). The authors are grateful to Professor Jianming Gu for help with the crystal structure analysis.

References

Bruck, E., Elbert, A., Fischer, R. & Krueger, S. (2009). Crop Prot. 28, 838-844.
Campbell, A. C., Maidment, M. S., Pick, J. H. & Stevenson, D. F. M. (1985). J. Chem. Soc. Perkin Trans. 1, pp. 1567-1576.  [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Fischer, R., Bretschneider, T., Lehr, S., Arnold, C., Dittgen, J., Feucht, D., Kehne, H., Malsam, O., Rosinger, C. H., Franken, E. M. & Goergens, U. (2010). US Patent No. 20100279873A1.
Fischer, R. & Weiss, H. C. (2008). Bayer CropSci. J. 61, 127-140.  [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Maus, C. (2008). Bayer CropSci. J. 61, 159-180.  [ChemPort]
Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Schobert, R. & Schlenk, A. (2008). Bioorg. Med. Chem. 16, 4203-4221.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wang, Z. C., Xu, B. R. & Cheng, J. L. (2011). Chin. J. Struc. Chem. 30, 1675-1679.  [ChemPort]
Zhao, J. H., Zhang, J. G., Xu, B. R., Wang, Z. C., Cheng, J. L. & Zhu, G. N. (2012). J. Agric. Food Chem. 60, 4779-4787.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1064-o1065   [ doi:10.1107/S160053681301430X ]

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