Crystal structure of (±)-(3aR,5R,8bR)-5-hydroperoxy-2-phenyl-6-tosyl-4,5,6,8b-tetrahydropyrrolo[3,4-e]indole-1,3(2H,3aH)-dione

The title compound, C₂₃H₂₀N₂O₆S, crystallizes as a racemate in the space group P-1, with an overall L- or J-shape to each molecule. Centrosymmetric pairs of molecules are tandem hydrogen bonded between the hydroperoxy H atom and carbonyl O atom. A different centrosymmetric pairing has stacked S-tolyl rings, and a third pairing is L,J-interlocked by the short leg. Except for stacked tolyl pairs, neighboring π-systems are much closer to orthogonal than coaxial. The title compound is the first example of a hydroperoxide obtained from the autoxidation of a Diels-Alder adduct of a 2-vinylpyrrole.