(E)-N-(6-Chloro-3-pyridylmethyl)-N-ethyl-N′-methyl-2-nitroethylene-1,1-diamine

In the title compound, C11H15ClN4O2, the amino group is involved in intra- and intermolecular N—H⋯O hydrogen bonds. The former contributes to the molecular conformation, while the latter link the molecules into centrosymmetric dimers. The crystal structure also exhibits weak intermolecular C—H⋯O interactions.

In the title compound, C 11 H 15 ClN 4 O 2 , the amino group is involved in intra-and intermolecular N-HÁ Á ÁO hydrogen bonds. The former contributes to the molecular conformation, while the latter link the molecules into centrosymmetric dimers. The crystal structure also exhibits weak intermolecular C-HÁ Á ÁO interactions.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2407). Nitenpyram is a new chloro-nicotine type insecticide (Wang et al., 2001) possessing a wide spectum of useful properties (Isao et al., 1993). We report here the crystal structure of the title compound (I).
In (I) (Fig. 1), all bond lengths and angles are in agreement with those reported for the related structures (Jiang et al., 2007;Xia et al., 2007). The pyridine ring and plane N2/N3/C9/C11 form a dihedral angle of 48.8 (2)°. The amino group is involved in intra-and intermolecular N-H···O hydrogen bonds (Table 1). The intermolecular N-H···O hydrogen bonds link the molecules into centrosymmetric dimers. The crystal packing exhibits also weak intermolecular C-H···O interactions (Table 1).

S2. Experimental
A solution comprising N-((6-chloropyridin-3-yl)methyl)ethanamine(0.1 mol) in trichloromethane(30 ml) was slowly added from a dropping-funnel to a mixture of 1,1,1-trichloro-2-nitro-ethane(0.15 mol), trichloromethane(30 ml) and an aqueous solution of sodium carbonate(40%, 53 g) in a flask equipped with stirrer and reflux condenser. After the mixture was stirred for 1 h while maintaining the temperature at 273-280k, an aqueous solution of methylamine(30%, 30 g) was then added dropwise, followed by a two hours stirring at room temperature. The reaction mixture were extracted with trichloromethane, the title compound (16.2 g, yield 60%) could be afforded after ethyl oxide was added to the concentration remnants on cooling. The single-crystal suitable for X-ray measurements was obtained by recrystallization from trichloromethane-ethyl acetate(1:1) at room temperature.

S3. Refinement
H atoms were positioned geometrically and allowed to ride on their parent atoms, with N-H and C-H distances of 0.86 and 0.93-0.97 Å, respectively, and with U iso (H) = 1.2U eq (C, N) for the aryl, methylene and N H atoms and 1.5U eq (C) for the methyl H atoms.  The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level. 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.