N-(2-Chloroquinolin-3-ylmethylene)aniline

The title compound, C16H11ClN2, displays a trans configuration across the C=N bond and a transoid arrangement across the quinoline ring and the azomethine C atom. This arrangement facilitates C—H⋯Cl interactions. The packing in the crystal structure is due to intermolecular C—H⋯π and Cl⋯π (3.52 and 3.84 Å) interactions. The dihedral angle between the least-squares planes of 2-chloroquinoline and phenylamine is 16.61 (2)°.

The title compound, C 16 H 11 ClN 2 , displays a trans configuration across the C N bond and a transoid arrangement across the quinoline ring and the azomethine C atom. This arrangement facilitates C-HÁ Á ÁCl interactions. The packing in the crystal structure is due to intermolecular C-HÁ Á Á and ClÁ Á Á (3.52 and 3.84 Å ) interactions. The dihedral angle between the least-squares planes of 2-chloroquinoline and phenylamine is 16.61 (2) .

D-HÁ
Many schiff bases have been synthesized from 2-chloro-3-formyl-quinoline (Meth-Cohn & Narine, 1978), for studying nonlinear Optical phenomenon arising due to the extended conjugation within the molecule. It is of interest to know the conformation around the azomethine double bond which restricts the free rotation and causes changes in dipole moment manifestations.

Experimental
A mixture of 2-chloro-3-formyl-quinoline (1.064 g, 0.004 mol) and aniline (0.37 ml,0.004 mol) in ethanol-acetic acid mixture (20 ml, 2:1) was stirred at room temperature for 6 h. After the completion of the reaction (6 h), the separated solid was filtered and washed with excess of cold alcohol·It was dried and crystallized from ethanol (yield = 92%, M·P=435 K).
Colourless rectangular crystals were grown from benzene and etyl acetate solvents (1:1, v/v) by slow evaporation method at room temperature.

Refinement
All H atoms atoms were located in difference fourier map and refined isotropically, with U iso (H)=1.2U eq (C). Fig. 1. ORTEP diagram of the molecule in asymmetric unit with 50% probability displacement ellipsoids showing the atom-numbering scheme and C-H···Cl interaction.