Acrinathrin: (S)-cyano­(3-phen­oxy­phenyl)methyl (Z)-(1R,3S)-2,2-dimethyl-3-{2-[2,2,2-trifluoro-1-(trifluoro­methyl)eth­oxy­carbon­yl]vin­yl}cyclo­propane-1-carboxyl­ate

Hojin Yang; Tae Ho Kim; Ki-Min Park; Jineun Kim

doi:10.1107/S1600536811014760

. 2011 Apr 29;67(Pt 5):o1275. doi: 10.1107/S1600536811014760

Acrinathrin: (S)-cyano(3-phenoxyphenyl)methyl (Z)-(1R,3S)-2,2-dimethyl-3-{2-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxycarbonyl]vinyl}cyclopropane-1-carboxylate

Hojin Yang ^a, Tae Ho Kim ^a,^*, Ki-Min Park ^a, Jineun Kim ^a,^*

PMCID: PMC3089073 PMID: 21754558

Abstract

In the title compound, C₂₆H₂₁F₆NO₅, the dihedral angle between the cyclopropane ring plane and the vinyl group plane is 79.3 (3)°. The dihedral angle between the benzene and phenyl ring planes in the phenoxybenzyl group is 82.7 (1)°. In the crystal structure, weak intermolecular C—H⋯π interactions and C—H⋯F hydrogen bonds contribute to the stabilization of the packing.

Related literature

For information on the insecticidal activity of the title compound, see: Vilchez et al. (1997 ▶). For related crystal structures, see: Owen (1976 ▶); Babin et al. (1992 ▶); Lei et al. (2001 ▶).

Experimental

Crystal data

C₂₆H₂₁F₆NO₅
M _r = 541.44
Orthorhombic,
a = 7.4932 (2) Å
b = 9.2679 (2) Å
c = 36.9165 (8) Å
V = 2563.71 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 173 K
0.17 × 0.14 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.979, T _max = 0.984
24962 measured reflections
3634 independent reflections
2868 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.099
S = 1.06
3634 reflections
345 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014760/wn2431sup1.cif

e-67-o1275-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014760/wn2431Isup2.hkl

e-67-o1275-Isup2.hkl^{(178.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C21–C26 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯F3ⁱ	0.95	2.45	3.200 (4)	135
C17—H17⋯Cg1ⁱⁱ	0.95	2.51	3.421 (1)	161

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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 (grant No. 2010-0009089).

supplementary crystallographic information

Comment

Acrinathrin (systematic name: (S)-α-cyano-3-phenoxybenzyl (Z)-(1R,3S)-2,2-dimethyl-3-[2- (2,2,2-trifluoro-1-trifluoromethylethoxycarbonyl)vinyl] cyclopropanecarboxylate), is a synthetic pyrethroid with high insecticidal activity aganist a wide range of insect pests (Vilchez et al., 1997). However its crystal structure has not yet been reported.

In the title compound (Scheme 1, Fig. 1), the absolute configurations for the three chiral centres of the molecule have been determined using the information provided by the Dr Ehrenstorfer GmbH Company. The dihedral angle between the cyclopropane ring plane and the vinyl group plane is 79.3 (3)°. The dihedral angle between the benzene and phenyl ring planes in the phenoxybenzyl group is 82.7 (1)°. All bond lengths and bond angles are normal and comparable to those observed in similar crystal structures (Lei et al., 2001).

In the crystal structure (Fig. 2) weak C—H···F hydrogen bonds are observed (Table 1). Weak intermolecular C—H···π interactions also exist [C17···Cg1ⁱⁱ 3.421 (1) Å. Cg1 is the centroid of the C21–C26 ring. (Symmetry codes: (ii) x + 1, y, z). These intermolecular interactions may contribute to the stabilization of the packing.

Experimental

The title compound was purchased from the Dr Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.