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3-(2-Chlorobenzylidene)-5-( p -tolyl)furan-2(3 H )-one ( 1 ), C 18 H 13 ClO 2 , crystallizes with  Z  = 8 and  Z′  = 2, and the structure at 100 K has orthorhombic ( Pna 2 1 ) 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.

Structure, Z′ = 2 Crystal Packing Features of 3-(2-Chlorobenzylidene)-5-(p-tolyl)furan-2(3H)-one