Crystal structure of (1S,2R,6R,7R,8S,12S)-4,10,17-triphenyl-15-thia-4,10-diazapentacyclo[5.5.5.0¹,¹⁶.0²,⁶.0⁸,¹²]heptadeca-13,16-diene-3,5,9,11-tetronep-xylene hemisolvate

The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule 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 bi-cyclo-[2.2.2]octene core, forming chains along [001].