N-(2-Chlorophenyl)succinimide

In the title compound, C10H8ClNO2, the dihedral angle between the aromatic benzene ring and the imide segment is 69.5 (1)°. In the crystal structure, molecules are linked by very weak C—H⋯π interactions along the [001] direction.

In the title compound, C 10 H 8 ClNO 2 , the dihedral angle between the aromatic benzene ring and the imide segment is 69.5 (1) . In the crystal structure, molecules are linked by very weak C-HÁ Á Á interactions along the [001] direction.

Related literature
For our study of the effect of ring and side-chain substitutions on the structures of this class of compounds, see: Gowda et al. (2007); Saraswathi et al. (2010a,b).
Cg1 is the centroid of the C1-C6 ring.
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: BX2270).

Comment
The amide moiety is an important constituent of many biologically significant compounds. As a part of studying the effect of ring and side chain substitutions on the structures of this class of compounds (Gowda et al., 2007;Saraswathi et al., 2010a,b), the crystal structure of N,N-(2-chlorophenyl)succinimide has been determined ( Fig. 1). In the structure of the title compound, C 10 H 8 ClNO 2 , the molecule is non-planar with the benzene and pyrrolidine rings tilted by 69.5 (1)° with respect to one another. In the crystal structure, the molecules are linked by weak C-H···π interactions.

Experimental
The solution of succinic anhydride (2.5 g) in toluene (25 ml) was treated dropwise with the solution of 2-chloroaniline (2.5 g) also in toluene(20 ml) with constant stirring. The resulting mixture was stirred for about one hour 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 2-chloroaniline. The resultant solid N-(2-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. N-(2-chlorophenyl)succinamic acid was then heated for 2 hours and then allowed to cool slowly to room temperature to get crystals of N-(2-chlorophenyl)succinimide. The purity of the compound was checked and characterized by its infrared spectra.
The prism like colourless single crystals of the compound used in X-ray diffraction studies were grown in ethanolic solution by a slow evaporation at room temperature.

Refinement
The H atoms were positioned with idealized geometry using a riding model with C-H in the range 0.93-0.97 Å. U iso (H) values were set equal to 1.2U eq (parent atom).   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.
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.