(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-p-tolylcyclopropanecarboxamide

There are two molecules in the asymmetric unit of the title compound, C16H17ClF3NO. The benzene ring in each molecule makes a dihedral angle of 66.6 (3)° [116.3 (4)° in the second molecule] with the plane of the cyclopropane ring. The F atoms of the CF3 groups are disordered equally over two positions. The amide hydrogen is linked with the amide oxygen in another molecule by an intermolecular N—H⋯O hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N—H⋯O hydrogen bonds.

There are two molecules in the asymmetric unit of the title compound, C 16 H 17 ClF 3 NO. The benzene ring in each molecule makes a dihedral angle of 66.6 (3) [116.3 (4) in the second molecule] with the plane of the cyclopropane ring. The F atoms of the CF 3 groups are disordered equally over two positions. The amide hydrogen is linked with the amide oxygen in another molecule by an intermolecular N-HÁ Á ÁO hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N-HÁ Á ÁO hydrogen bonds. 137 restraints H-atom parameters constrained Á max = 0.60 e Å À3 Á min = À0.45 e Å À3 Table 1 Hydrogen-bond geometry (Å , ). Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Related literature
(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-p-tolylcyclopropanecarboxamide  The structure in this article containing both of two active parts is expected to show some insecticide activity. The present Xray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound, (I). In this paper, the title compound, (E)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N-p-tolylcyclopropane-carboxamide, (I), was synthesized and the structure of (I) is illustrated in Fig. 1. The dihedral angles between the benzene moiety and the cyclopropane group is 66.6 (3)°. The amide hydrogen is linked with the amide oxygen in an adjoining molecule by an intermolecular N-H···O hydrogen bond. The packing can be described as a dimeric arrangement of molecules linked through N-H···O hydrogen bonds (Table 1).

Refinement
H atoms were positioned geometrically with C-H = 0.92-0.98 Å and refined using riding model with U iso (H) = 1.2Ueq(carrier). The amine H atom was located from difference map and refined isotropically. The disordered CF 3 was allowed to rotate about its C-C axis.

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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 > 2sigma(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.