Methyl (E)-3-(2-formylphenoxy)acrylate

In the title compound, C11H10O4, the methyl acrylate substituent adopts an extended E conformation with all torsion angles close to 180°. The conformation of the keto group with respect to the olefinic double bond is typically S-trans. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) graph-set motif. The dimers are further linked via C—H⋯O hydrogen bonds, forming chains along [001], which enclose R 3 2(16) graph-set ring motifs. The keto group O atomaccepts two C—H⋯O interactions.

In the title compound, C 11 H 10 O 4 , the methyl acrylate substituent adopts an extended E conformation with all torsion angles close to 180 . The conformation of the keto group with respect to the olefinic double bond is typically Strans. In the crystal, molecules are linked via pairs of C-HÁ Á ÁO hydrogen bonds, forming inversion dimers with an R 2 2 (8) graph-set motif. The dimers are further linked via C-HÁ Á ÁO hydrogen bonds, forming chains along [001], which enclose R 3 2 (16) graph-set ring motifs. The keto group O atomaccepts two C-HÁ Á ÁO interactions.

Experimental
Supporting information for this paper is available from the IUCr electronic archives (Reference: SU2732).

Comment
Cinnamic acid derivatives have received attention in medicinal research as traditional as well as recent synthetic antitumor agents (De et al., 2011). They also posses significant antibacterial activities against staphylococcus aureus (Xiao et al., 2008). Different substitutions on the basic moiety lead to various pharmacological activities, such as antioxidant, hepatoprotective, anxiolytic, insect repellent, antidiabetic, and anticholesterolemic (Sharma, 2011).
In the title molecule, Fig. 1, the methyl acrylate group is essentially planar, with a maximum deviation of 0.0264 (19) Å for atom C9. Its mean plane forms a dihedral angle of 31.74 (6)° with the benzene ring (C2-C7). The molecular dimensions are in excellent agreement with the those reported for a closely related compound (Karthikeyan et al., 2012).
The configuration of the keto group with respect to the olefinic double bond is typically S-trans, with the O2═C10-C9═C8 torsion angle = 178.78 (19)°. The methyl acrylate group adopts an extended E conformation with torsion angles The extended conformation is supported by the fact that the bond angles involving carbonyl O atoms are invariably enlarged (Dunitz & Schweizer, 1982).

Experimental
Salicylaldehyde (1 mmol) was dissolved in an aqueous solution of K 2 CO 3 (1 mmol) and methyl propiolate (1 mmol) was added. The reaction mixture was stirred vigorously at room temperature. A turbid solution was formed by consumption of salicylaldehyde (monitored by TLC) in 5 min, the reaction mixture then became clear. The title compound was precipitated as a solid in water. The product was isolated by filtration without further purification [Yield 75%]. Block-like colourless crystals were obtained by slow evaporation of a solution in ethylacetate.

Refinement
The H atoms could all be located in difference electron-density maps. In the final cycles of refinement they were treated as riding atoms: C-H = 0.93 and 0.96 Å for CH and CH 3 H atoms, respectively, with U iso (H) = 1.5 U eq (C-methyl) and = 1.2U eq (C) for other H atoms.

Figure 1
The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
The crystal packing of the title compound viewed along the b axis, showing the formation of the R 2 2 (8) graph-set motif. The dimers are further consolidated by R 2 3 (16) graph-set ring motifs. Hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).) 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.