3-(2-Chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethyl-N-[3-(trifluoromethyl)phenyl]cyclopropanecarboxamide

In the title molecule, C16H14ClF6NO, the cyclopropane ring forms a dihedral angle of 70.82 (18)° with the benzene ring. The torsion angles about the ethylene and amide bonds are −2.2 (5) (Cl—C—C—C) and 0.8 (5)° (O—C—N—C). A supramolecular chain propagated by glide symmetry along [001] and mediated by N—H⋯O hydrogen bonds is observed in the crystal packing.

In the title molecule, C 16 H 14 ClF 6 NO, the cyclopropane ring forms a dihedral angle of 70.82 (18) with the benzene ring. The torsion angles about the ethylene and amide bonds are À2.2 (5) (Cl-C-C-C) and 0.8 (5) (O-C-N-C). A supramolecular chain propagated by glide symmetry along [001] and mediated by N-HÁ Á ÁO hydrogen bonds is observed in the crystal packing.

Guo-Wu Rao, Xiao-Min Li and Na-Bo Sun Comment
Pyrethroids have a high potential for biological activity with low toxicity and good environmental compatibility. These have been widely used in pesticides (Chen et al., 1991;Sun et al., 2007Sun et al., , 2008. In continuation of our studies of biological activities in pyrethroids, we have obtained a colourless crystalline compound, (I). The structure was confirmed by single-crystal X-ray diffraction.

Experimental
The title compound was synthesized according to the literature procedure (Sun et al., 2007). A solution of the compound in ethanol was concentrated gradually at room temperature to afford colourless blocks.

Refinement
The H-atoms were placed in calculated positions [N-H = 0.86 Å; C-H = 0.93 to 0.98 Å, U iso (H) = 1.2U eq (C,N)] and were included in the refinement in the riding model approximation. The CF 3 group was disordered and modelled over two positions of equal weight.  The molecular structure of (I), shown with 30% probability displacement ellipsoids. The F atoms of the CF 3 group have 50% occupancy factors.  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Occ. (