Noland, W. E.; Kroll, N. J.; Huisenga, M. P.; Yue, R. A.; Lang, S. B.; Klein, N. D.; Tritch, K. J. Acta Crystallogr. Sect. E, 2014, 70, 550.
The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels–Alder reaction of 2-(α-styryl)thiophene with N-phenylmaleimide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene molecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bicyclo[2.2.2]octene core, forming chains along .