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Volume 69 
Part 3 
Page o453  
March 2013  

Received 30 January 2013
Accepted 22 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.122
Data-to-parameter ratio = 17.9
Details
Open access

(1'S,4'S)-5-(2,5-Dimethylphenyl)-4'-methoxy-6-oxa-3-azaspiro[bicyclo[3.1.0]hexane-2,1'-cyclohexan]-4-one

aCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310032, People's Republic of China, and bInstitute 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, C18H23NO3, the cyclohexane ring has a chair conformation. The oxirane plane (OCC) makes a dihedral angle of 76.15 (13)° with that of the pyrrolidine ring to which it is fused. The mean plane of the cyclohexane ring and the benzene ring are almost normal to the pyrrolidine ring, with dihedral angles of 88.47 (8) and 77.85 (8)°, respectively. In the crystal, molecules are linked via pairs of N-H...O hydrogen bonds, forming inversion dimers. These dimers are linked via pairs of C-H...O hydrogen bonds, forming chains along the a-axis direction.

Related literature

For the pesticide spirotetramat, 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.]). 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
  • C18H23NO3

  • Mr = 301.37

  • Monoclinic, P 21 /n

  • a = 9.1932 (4) Å

  • b = 9.8139 (4) Å

  • c = 17.6979 (7) Å

  • [beta] = 91.198 (1)°

  • V = 1596.38 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.53 × 0.38 × 0.36 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 = 0.946, Tmax = 0.970

  • 15333 measured reflections

  • 3629 independent reflections

  • 2407 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.122

  • S = 1.00

  • 3629 reflections

  • 203 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.86 2.25 3.0760 (17) 160
C9-H9A...O2ii 0.97 2.56 3.413 (2) 147
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+2, -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: SU2559 ).


Acknowledgements

This project was supported by grants from the National Natural Science Foundation of China (No. 31101470) and the Educational Commission of Zhejiang Province (Y201224393). The authors are grateful to Professor Jianming Gu for the crystal analysis.

References

Bruck, E., Elbert, A., Fischer, R. & Krueger, S. (2009). Crop Prot. 28, 838-844.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o453  [ doi:10.1107/S1600536813005138 ]

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