The title compounds, C21H16O2S2(I) and C25H20O2(II), are products of a tandem `pincer' Diels–Alder reaction consisting of [2 + 2] cycloadditions between benzo[c]furan and cyclopentanone. Each comprises a fused tetracyclic ring system containing two five-membered rings (inenvelopeconformations with the O atom as the flap) and six-membered rings (inboatconformations). In addition, two thiophene rings in (I) and two phenyl rings in (II) are attached to the tetracyclic ring system. The cyclopentanone ring adopts atwistedconformation in (I) and anenvelopeconformation in (II). In (I), the thiophene rings are positionally disordered over two sets of sites, with occupancy ratios of 0.901 (2):0.099 (2) and 0.666 (2):0.334 (2). In (II), the oxygen atom of the cyclopentanone ring is rotationally disordered over two sites with an occupancy ratio of 0.579 (4):0.421 (4). The molecular structure of (I) is stabilized by an intramolecular C—H...O hydrogen bond, which generates anS(7) ring motif. In the crystal, the molecules are linkedviaweak C—H...O hydrogen bonds, which generateR22(16) ring motifs in (I) andC(8) chains in (II). In both structures, the crystal packing also features C—H...π interactions. The crystal studied of compound (I) was twinned by non-merohedry. The twin component is related by the twin law [−1 0 0 −0.101 1 −0.484 0 0 −1] operated by a twofold rotation axis parallel to thebaxis. The structure of (I) was refined with a twin scale factor of 0.275 (2).
Crystal structures and conformations of two Diels–Alder adduct derivatives: 1,8-bis(thiophen-2-yl)-14-oxatetracyclo[6.5.1.02,7.09,13]tetradeca-2(7),3,5-trien-10-one and 1,8-diphenyl-14-oxatetracyclo[6.5.1.02,7.09,13] tetradeca-2,4,6-trien-10-one