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

Kim, T.H.; Park, K.-M.; Jeon, Y.; Kim, J.

doi:10.1107/S1600536812040767

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 (C-C) = 0.003 Å
R = 0.043
wR = 0.096
Data-to-parameter ratio = 10.7
Details

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

Tae Ho Kim,^a Ki-Min Park,^a ^* Youngeun Jeon ^a and Jineun Kim ^a ^*

^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-HO 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). For a related structure, see: Yang et al. (2011).

Experimental

Crystal data

C₂₂H₂₆O₃
M_r = 338.43
Monoclinic, P 2₁
a = 7.8438 (14) Å
b = 11.555 (2) Å
c = 10.9649 (18) Å
= 108.375 (3)°
V = 943.2 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.975, T_max = 0.992
9877 measured reflections
2458 independent reflections
2156 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.096
S = 1.04
2458 reflections
230 parameters
1 restraint
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C7-H7AO3ⁱ	0.99	2.71	3.516 (3)	139
C11-H11Cgⁱⁱ	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); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998); 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.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, H., Kim, T. H., Park, K.-M. & Kim, J. (2011). Acta Cryst. E67, o1275.

organic compounds