2-[(4-Formylphenyl)(hydroxy)methyl]acrylonitrile

In the title compound, C11H9NO2, the mean planes formed by the phenyl and acryl group are almost orthogonal to each other, with a dihedral angle of 88.61 (7)°. The carbonitrile side chain is almost linear, the C—C—N angle being 179.54 (16)°. In the crystal, molecules are linked by intermolecular O—H⋯O interactions into infinite chains running parallel to the b axis.

In the title compound, C 11 H 9 NO 2 , the mean planes formed by the phenyl and acryl group are almost orthogonal to each other, with a dihedral angle of 88.61 (7) . The carbonitrile side chain is almost linear, the C-C-N angle being 179.54 (16) . In the crystal, molecules are linked by intermolecular O-HÁ Á ÁO interactions into infinite chains running parallel to the b axis.

Comment
Acrylonitrile derivatives have been shown to possess antitubercular and antitumour activities (Ohsumi et al., 1998).
In the title compound ( Fig. 1), the mean planes formed by the phenyl ring C2-C7 and acryl group (N1/C8-C11) are almost orthogonal to each other with a dihedral angle 88.61 (7)°. The bond length C9-C11 [1.4338 (18) Å] is significantly shorter than the expected value for a C-C single bond because of conjugation effects (Nizam Mohideen et al., 2007).
The mean plane of C2-C1-O1 is slightly twisted out of the mean plane of phenyl ring C2-C7 with a dihedral angle 2.62 (9)°. The carbonitrile side chain (C9-C11-N1) is almost linear, with the angle around central carbon atom being 179.54 (16)°. The title compound exhibits structural similarities with closely related structures (Cobo et al.2005, Nizam Mohideen et al.2007).
In the title compound, the crystal packing is stabilized by O2-H2···O1 intermolecular interactions which link the molecules into infinite chains running parallel to the b-axis (Tab. 1 & Fig. 2).

Experimental
To a reaction mixture of terephthalaldehyde (1 mmol) and acrylonitrile (2 mmol) was added a catalytic quantity of 1,4diazabicyclo[2.2.2]octane (10-15 mol %). The reaction mixture was left standing at room temperature in a stoppered sample flask. The progress of the reaction was monitored by Thin Layer Chromatography (TLC) over a period of several days.
After 6 days the TLC revealed the presence of a product. The reaction mixture was dissolved in ethyl acetate and washed with aqueous HCl solution (0.25 M) and water followed by brine solution. The organic layer was separated and dried over sodium sulfate, filtering and evaporation of the organic solvent under reduced pressure. The product was seperated by flash column chromatography using hexane and ethyl acetate (4:1) as an eluent to give colorless solid. The product was dissolved in chloroform and heated for two minutes. The resulting solution was subjected to crystallization by slow evaporation of the solvent resulting in single crystals suitable for XRD studies.

Refinement
The hydrogen atoms were placed in calculated positions with C-H = 0.93 to 0.98 Å and O-H = 0.82 Å and refined in the riding model with isotropic displacement parameters: U iso (H) = 1.2U eq (C) or 1.5U eq (O).   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 Rfactors(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.