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Volume 68 
Part 11 
Page o3060  
November 2012  

Received 25 September 2012
Accepted 27 September 2012
Online 3 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.096
Data-to-parameter ratio = 10.7
Details
Open access

Bioresmethrin: (5-benzylfuran-3-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
Correspondence e-mail: kmpark@gnu.ac.kr, jekim@gnu.ac.kr

In the title compound, C22H26O3, the dihedral angle between the cyclopropane ring and the plane of the vinyl group is 88.2 (2)°. The dihedral angle between the phenyl and furan rings is 86.09 (8)°. In the crystal, weak intermolecular C-H...[pi] contacts together with very weak C-H...O hydrogen bonds stack the molecules along the a axis.

Related literature

For information on the insecticidal activity of the title compound, see: Hill et al. (1993[Hill, A. S., McAdam, D. P., Edward, S. L. & Skerritt, J. H. (1993). J. Agric. Food Chem. 41, 2011-2018.]). For a related structure, see: Yang et al. (2011[Yang, H., Kim, T. H., Park, K.-M. & Kim, J. (2011). Acta Cryst. E67, o1275.]).

[Scheme 1]

Experimental

Crystal data
  • C22H26O3

  • Mr = 338.43

  • Monoclinic, P 21

  • a = 7.8438 (14) Å

  • b = 11.555 (2) Å

  • c = 10.9649 (18) Å

  • [beta] = 108.375 (3)°

  • V = 943.2 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.33 × 0.28 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.992

  • 9877 measured reflections

  • 2458 independent reflections

  • 2156 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.096

  • S = 1.04

  • 2458 reflections

  • 230 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C7-H7A...O3i 0.99 2.71 3.516 (3) 139
C11-H11...Cgii 0.95 2.63 3.559 (3) 167
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany..]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5266 ).


Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2010-0009089).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany..
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hill, A. S., McAdam, D. P., Edward, S. L. & Skerritt, J. H. (1993). J. Agric. Food Chem. 41, 2011-2018.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Yang, H., Kim, T. H., Park, K.-M. & Kim, J. (2011). Acta Cryst. E67, o1275.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3060  [ doi:10.1107/S1600536812040767 ]

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