title: Crystal structure of (±)-(3aR,5R,8bR)-5-hydroper-oxy-2-phenyl-6-tosyl-4,5,6,8b-tetra-hydro-pyrrolo-[3,4-e]indole-1,3(2H,3aH)-dione.
abstract: The title compound, C23H20N2O6S, crystallizes as a racemate in the space group P-1, with an overall L- or J-shape to each mol-ecule. Centrosymmetric pairs of mol-ecules are tandem hydrogen bonded between the hydro-per-oxy H atom and carbonyl O atom. A different centrosymmetric pairing has stacked S-tolyl rings, and a third pairing is L,J-inter-locked 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 hydro-peroxide obtained from the autoxidation of a Diels-Alder adduct of a 2-vinyl-pyrrole.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Wayland E
authors.initials: WE
authors.lastname: Noland
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Glen C
authors.initials: GC
authors.lastname: Gullickson
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Rozalin R
authors.initials: RR
authors.lastname: Dickson
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Leah L
authors.initials: LL
authors.lastname: Groess
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.
authors.forename: Kenneth J
authors.initials: KJ
authors.lastname: Tritch
keywords: autoxidation; crystal structure; cyclo­addition; hydro­peroxide; indole; pyrrole