Crystal structure of rac-(3a'R,9a'R)-3a'-(indol-3-yl)-1′,2′,3′,3a',4′,9a'-hexa­hydro­spiro­[cyclo­pentane-1,9′-penta­leno[1,2-b]indole] p-xylene hemisolvate

Noland, W. E.; Worth, M. A.; Schneerer, A. K.; Paal, C. L.; Tritch, K. J. Acta Crystallogr. Sect. E 2015, 71, 516.

The title compound, C26H26N2·0.5C8H10, is the first reported characterized 2:2 product from acid-catalyzed condensation of indole with cyclo­penta­none and no other 2:2 products were observed. Recrystallization from p-xylene gave the title hemisolvate with the p-xylene mol­ecule located about an inversion center. The terminal penta­lene ring is envelope-flap disordered at the C atom farthest from the skeletal indole unit, with a refined occupancy ratio of 0.819 (4):0.181 (4). The major component has this C atom bent away from the spiro-fused cyclo­pentane ring. In the crystal, mol­ecules are connected by N—H⋯π inter­actions, forming chains along [100], and N—H⋯π and C—H⋯π inter­actions, forming chains along [001], which results in the formation of slabs parallel to (010).