3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one (1), C18H13ClO2, crystallizes with Z = 8 and Z' = 2, and the structure at 100 K has orthorhombic (Pna21) symmetry. Each kind of molecule takes part in π-π stacking interactions to form infinite chains parallel to the c axis. We believe that the existence of two forms can be explained by the probable rotation around a single C-C bond. The quantum chemical modeling reveals that these molecules are almost equivalent energetically, and they can be described as the two most stable conformers (rotamers) with a minor rotational barrier of about 0.67 kcal/mol.
Keywords: 3-arylidene-5-arylfuran2(3H)-one; crystal structure; crystallographically independent forms; quantum chemical modeling; rotamers; rotational barrier.