N-Phenylsuccinamic acid

In the crystal structure of the title compound, C10H11NO3, the conformations of N—H and C=O bonds in the amide segment are anti to each other. Further, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the adjacent –CH2 groups. The C=O and O—H bonds of the acid group are in syn positions with respect to each other. In the crystal, the molecules are packed into infinite chains along the a axis through intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

In the crystal structure of the title compound, C 10 H 11 NO 3 , the conformations of N-H and C O bonds in the amide segment are anti to each other. Further, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to each other and to the adjacent -CH 2 groups. The C O and O-H bonds of the acid group are in syn positions with respect to each other. In the crystal, the molecules are packed into infinite chains along the a axis through intermolecular N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds.

Related literature
For our studies of the effect of substituents on the structures of anilides, see: Gowda et al. (2009Gowda et al. ( , 2010a. For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976). For the packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994).  Table 1 Hydrogen-bond geometry (Å , ).
BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2265).   Fig.2).
The modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). The packing of molecules involving dimeric hydrogen bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed (Jagannathan et al., 1994).

Experimental
The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of aniline (0.01 mole) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about one h and set aside for an additional hour at room temperature for completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted aniline. The resultant solid N-(phenyl)succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.
Prism like colorless single crystals used in x-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement
The H atoms of the NH and OH group were located in a difference map and later restrained to the distance N-H = 0.86 (2) Å and O-H = 0.82 (2) Å. The other 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 times of the U eq of the parent atom). Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.