N-Acryloylphenylalanine

The title compound, C12H13NO3, was prepared by the nucleophilic substitution reaction of acryloyl chloride with glycylglycine. In the crystal structure, intermolecular N—H⋯O, O–H⋯O and C—H⋯O hydrogen bonds link the molecules into a three-dimensional network.

The title compound, C 12 H 13 NO 3 , was prepared by the nucleophilic substitution reaction of acryloyl chloride with glycylglycine. In the crystal structure, intermolecular N-HÁ Á ÁO, O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds link the molecules into a three-dimensional network.
its synthesis and crystal structure.
In the molecule of the title compound ( Fig. 1) the bond lengths and angles are within normal ranges (Allen et al., 1987).
In the crystal structure, intermolecular N-H···O, O-H···O and C-H···O hydrogen bonds (Table 1) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in stabilization of the structure.

Experimental
For the preparation of the title compound, to a well stirred solutions of phenylalanie (2.5 g) in H 2 O (30 ml) and sodium hydroxide (0.66 g) in H 2 O (5 ml), acryloyl chloride (1.34 ml) containing diphenylpicrylhydrazyl polymerization inhibitor (0.01%) and sodium hydroxide solution (0.66 g) in H 2 O (5 ml) were added dropwise simultaneously over a 30 min period and the stirring was continued for another 1 h. The reaction mixture was kept at 273 K in an ice-water bath. The solution was acidified to pH = 2 with HCl (6 N). The resulting solid was filtered off, and crystallized from ethanol (95%) (yield; 61%, m.p.401-403 K).

Refinement
H atoms were positioned geometrically, with O-H = 0.82 Å (for OH), N-H = 0.86 Å (for NH) and C-H = 0.93, 0.98 and 0.97 Å for aromatic, methine and methylene H, respectively, and constrained to ride on their parent atoms with U iso (H) = xU eq (C,N,O), where x = 1.5 for OH H and x = 1.2 for all other H atoms. Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% 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 > 2sigma(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.