Ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate

In the title compound, C13H13NO3, the conformation across the C=C bond is synperiplanar, the torsion angle of the segment C(ring)—C=C—C(N) being 3.2 (5)°. In the crystal, molecules are linked into inversion dimers, arranged in a zigzag pattern, through two C—H⋯O interactions generating R 2 2(10) and R 2 2(14) motifs. These dimers are arranged in a zigzag pattern in the crystal structure. The molecules are further linked along the c axis through weak C—H⋯π interactions, and weak π⋯π interactions [centroid–centroid separation = 3.9986 (17) Å] are also observed.

In the title compound, C 13 H 13 NO 3 , the conformation across the C C bond is synperiplanar, the torsion angle of the segment C(ring)-C C-C(N) being 3.2 (5) . In the crystal, molecules are linked into inversion dimers, arranged in a zigzag pattern, through two C-HÁ Á ÁO interactions generating R 2 2 (10) and R 2 2 (14) motifs. These dimers are arranged in a zigzag pattern in the crystal structure. The molecules are further linked along the c axis through weak C-HÁ Á Á interactions, and weak Á Á Á interactions [centroid-centroid separation = 3.9986 (17) Å ] are also observed.

Related literature
For use of the title compound in the synthesis of prop-2enoylamides, see: Santos et al.. (2004). For use of the title compound in the synthesis of prop-2-enoates, see: Sousa et al. (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995 Table 1 Hydrogen-bond geometry (Å , ).
Ethyl-2-cyanoacrylate (0.81 g, 6.4 mmol) was added to the solution and the reaction mixture was heated to 120 °C for 10 h, cooled and filtered under vacuum to obtain the crude compound. This was further purified by column chromatography using petroleum ether: ethyl acetate (7:3) as eluent (Rf value = 0.69), to yield pale green colored crystals.

Refinement
The H atoms were positioned with idealized geometry using a riding model with C-H = 0.93-0.97 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times U eq of the parent atom).

Figure 4
Linking of molecules along the c axis through C-H···Cg interactions.  π-π stacking interactions observed in the crystal structure. H atoms are omitted for clarity.

Ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate
Crystal data where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.012 Δρ max = 0.18 e Å −3 Δρ min = −0.25 e Å −3 Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.