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

Noland, W. E.; Gullickson, G. C.; Dickson, R. R.; Groess, L. L.; Tritch, K. J. Acta Crystallogr. Sect. E, 2014, 70, 192.

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.