(1S R,3S R)-[(SR)-Cyano­(3-phenoxy­phen­yl)meth­yl] 3-[(Z)-2-chloro-3,3,3-trifluoro­prop-1-en­yl]-2,2-dimethyl­cyclo­propane-1-carboxyl­ate

Jing Cheng; Guangxiu Ju; Jinfeng Dong

doi:10.1107/S1600536808034855

. 2008 Nov 8;64(Pt 12):o2253. doi: 10.1107/S1600536808034855

(1S R,3S R)-[(SR)-Cyano(3-phenoxyphenyl)methyl] 3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate

Jing Cheng ^a, Guangxiu Ju ^a, Jinfeng Dong ^a,^*

PMCID: PMC2960082 PMID: 21581234

Abstract

In the crystal of the title compound, C₂₃H₁₉ClF₃NO₃, molecules are linked by one C—H⋯O hydrogen bond and two C—H⋯π interactions into a three-dimensional network.

Related literature

For the insecticidal activity of the title compound, see: Anadón et al. (2006 ▶). For the synthesis, see: Whittle (1991 ▶).

Experimental

Crystal data

C₂₃H₁₉ClF₃NO₃
M _r = 449.84
Monoclinic,
a = 34.7685 (13) Å
b = 7.0159 (3) Å
c = 18.6075 (7) Å
β = 102.113 (1)°
V = 4437.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.927, T _max = 0.957
18537 measured reflections
4361 independent reflections
2721 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.174
S = 1.03
4361 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034855/cs2097sup1.cif

e-64-o2253-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034855/cs2097Isup2.hkl

e-64-o2253-Isup2.hkl^{(213.8KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3ⁱ	0.98	2.39	3.218 (3)	142
C21—H21⋯O3	0.93	2.34	2.984 (3)	126
C19—H19C⋯O3	0.96	2.39	3.037 (3)	124
C5—H5⋯Cg1ⁱⁱ	0.93	2.94	3.721 (1)	143 (1)
C9—H9⋯Cg1ⁱⁱⁱ	0.93	3.06	3.768 (1)	134 (1)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.

Acknowledgments

The authors are grateful to Wuhan Science and Technology program (No. 200760423155) financial support.

supplementary crystallographic information

Comment

The title compound, also known as λ-cyhalothrin, exhibits wide-spectrum insecticidal activitiy and represents a good compromise between efficacy and toxicity [Anadón et al., 2006; Whittle, 1991]. In order to research into the relationship between structure and activity, we re-synthesized the title compound and report its crystal structure.

The two benzene rings (defined by atoms C1—C6 and C7—C12, respectively) connected via the O1 atom form a dihedral angle of 89.4 (1)° (Fig.1). The –CF3 group in this appears as a relative rare ordered one which may be due to a close approach of H21···F3 0.93/2.37 Å (idealized: 1.08/2.34 Å) (Table 1). No other unusual features are worth of mention.

In the crystal packing, the molecules at (x, y, z) and (-x + 2, -y + 1, z - 1) are linked together by C13—H13···O3ⁱ interactions (Table 1), forming a dimer. Further analysis (Spek, 2003) indicates that these dimers are joined by C—H···π interactions, forming a three-dimensional network (Fig.2). In more detail, one C—H···π interaction is C5—H5···Cg1ⁱⁱ [C5···Cg1=3.721 (1) Å, C5—H5···Cg1=142.8 (1)°, symmetry code: (ii) 3/2 - x, 1/2 + y, 1/2 - z, Cg1 is the centroid defined by phenyl C atoms C1 to C6] and the other one is C9—H9···Cg1ⁱⁱⁱ(C9···Cg1=3.768 (1) Å, C9—H9···Cg1=134.0 (1)°, symmetry code: (iii) x, y - 1,z].

Experimental

The title compound was synthesized according to a standard procedure (Whittle, 1991). Light blue crystals appropriate for data collection were obtained by slow evaporation of a 2-propanol solution at room temperature.