N-(3-Chlorophenyl)succinamic acid

In the title compound, C10H10ClNO3, the N—H and C=O bonds in the amide segment are trans to each other. In the crystal structure, the molecules are linked into infinite chains through intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

In the title compound, C 10 H 10 ClNO 3 , the N-H and C O bonds in the amide segment are trans to each other. In the crystal structure, the molecules are linked into infinite chains through intermolecular N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds.

Comment
As a part of studying the effect of ring and side chain substitutions on the structures of anilides (Gowda et al., 2009a,b;2010), the crystal structure of N-(3-chlorophenyl)succinamic acid (I) has been determined. The conformations of N-H and C=O bonds in the amide segment are anti to each other, similar to those observed in N-(2chlorophenyl)succinamic acid (II) (Gowda et al., 2009b) and N-(4-chlorophenyl)succinamic acid (III) (Gowda et al., 2009a) and N-(3-methylphenyl)succinamic acid (IV) (Gowda et al., 2010). But the conformation of the amide oxygen and the car- The conformation of the amide hydrogen is syn to the meta-Cl group in the benzene ring, similar to that of the ortho-Cl in (II), but contrary to the anti conformation observed between the amide hydrogen and the meta-methyl group in (IV).
The N-H···O and O-H···O intermolecular hydrogen bonds pack the mpolecules into infinite chains in the structure (Table 1, Fig.2).
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 m-chloroaniline (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 m-chloroaniline. The resultant solid N-(3-chlorophenyl)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. The plate 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 OH and NH group were located in a difference map and refined with a distance restraint of O-H = 0.82 (2) %A and N-H = 0.86 (2) %A. The other H atoms were positioned with idealized geometry using a riding model supplementary materials sup-2 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 labelling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.  Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Figures
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.