Methyl (2E)-2-cyano-3-(dimethylamino)prop-2-enoate

In the title compound, C7H10N2O2, the dimethylamino group is twisted slightly relative to the acrylate fragment, forming a dihedral angle of 11.6 (1)°. In the crystal, molecules are linked via pairs of bifurcated C—H/H⋯O hydrogen bonds, forming inversion dimers, which are further connected by C—H⋯N hydrogen bonds into chains along the a-axis direction.

In the title compound, C 7 H 10 N 2 O 2 , the dimethylamino group is twisted slightly relative to the acrylate fragment, forming a dihedral angle of 11.6 (1) . In the crystal, molecules are linked via pairs of bifurcated C-H/HÁ Á ÁO hydrogen bonds, forming inversion dimers, which are further connected by C-HÁ Á ÁN hydrogen bonds into chains along the a-axis direction.

Deshmukh Comment
Enamines are the multipurpose synthetic intermediates used for the synthesis of a variety of organic derivatives, bioactive natural products and their analogs (Huang et al., 2007;Michael et al., 1999).
In (I) (Fig.1), all bond lengths and angles are normal and correspond to those observed in the related structure (Gupta et al., 2007). The dihedral angle between dimethylamino and acrylate fragment is 11.6 (1)°. In the crystal, C3-H3···O1 and C4-H4A···O1 hydrogen bonds link molecules to form dimers. Dimers are further connected by C-H···N hydrogen bonds into chains along the a axis ( Fig. 2

Experimental
In a 50 ml round bottom flask the mixture of 5 mmole of methyl cyanoacetate and 5 mmole of dimethylformamide dimethyl acetal was stirred at room temperature for 1-1.5 h. After completion of reaction, the reaction mixture was poured on ice cold water and the separated solid was precipated after 15 minutes and recrystallized from ethanol. Yield: 87%; m.p. 378-380 K. IR(KBr): 2205, 1695, 1621, 1433, 1373, 1287, 1216 1/cm

Refinement
All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C-H distances of 0.93-0.96 Å and with U iso (H) = 1.2U eq (C) or 1.5U eq (methyl C).

Computing details
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009   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.