{5-Chloro-2-[(4-nitrobenzylidene)amino]phenyl}(phenyl)methanone

The molecule of the title Schiff base compound, C20H13ClN2O3, assumes an E configuration about the C=N bond. The aromatic rings of the nitrobenzene and chlorobenzene groups are twisted by 13.89 (13)° and form dihedral angles of 76.38 (13) and 84.64 (13)°, respectively, with the phenyl ring. In the crystal, molecules are linked into chains parallel to the b axis by C—H⋯π interactions.

The molecule of the title Schiff base compound, C 20 H 13 ClN 2 O 3 , assumes an E configuration about the C N bond. The aromatic rings of the nitrobenzene and chlorobenzene groups are twisted by 13.89 (13) and form dihedral angles of 76.38 (13) and 84.64 (13) , respectively, with the phenyl ring. In the crystal, molecules are linked into chains parallel to the b axis by C-HÁ Á Á interactions.

Experimental
Cg1 is the centroid of the C1-C6 ring.

Comment
Schiff bases are well known reaction products of aldehyde/ketone functionalities with amines and are considered as important ligands in coordination chemistry. They are also well known to possess a wide range of biological activities including antifungal, antiinflammatory, anti-HIV, antibacterial, herbicidal, antiproliferative, cytotoxic, anticonvulsant and anticancer activities (Khan et al., 2009;Gerdemann et al., 2002;Samadhiya & Halve, 2001;Mallikarjun & Sangamesh, 1997;Fioravanti et al., 1995;Solomon & Lowery, 1993). The title compound was prepared and crystallized during our ongoing research on bioactive compounds.

Experimental
The synthesis of title compound was carried out by refluxing a mixture of 4-nitrobenzaldehyde (1 mol) and 2-amino-5chlorobenzophenone (1 mol) in ethanol (50 ml) along with 3 drops of conc. H 2 SO 4 for 5 h at 70 °C. After cooling down to room temperature, the crystalline product was collected by filtration, washed with methanol and dried to afford the title compound in 85% yield. Recrystallization from methanol afforded yellow crystals found suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.

Refinement
H atoms were positioned geometrically with C-H = 0.93 Å, and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.