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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 ?-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.

SUBMITTER: Noland WE

PROVIDER: S-EPMC4257163 | biostudies-other | 2014 Oct

REPOSITORIES: biostudies-other

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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.

Noland Wayland E WE Gullickson Glen C GC Dickson Rozalin R RR Groess Leah L LL Tritch Kenneth J KJ

Acta crystallographica. Section E, Structure reports online 20140913 Pt 10

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 ...[more]

PMID: 25484649

Similar Datasets

(3aR*,5R*)-5-(4-Chloro-phen-yl)-1,2,3,3a-tetra-hydro-benzo[e]pyrrolo-[2,1-b][1,3]ox-azepin-10(5H)-one.

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Bioresearch of New 1H-pyrrolo[3,4-c]pyridine-1,3(2H)-diones.

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3-Benzyl-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa-hydro-1H-pyrrolo[3,4-b]quinoline.

Project description:In the title compound, C(31)H(30)N(2)O(2)S, the pyrrolidine ring adopts a twist conformation while the tetra-hydro-pyridine ring is in a half-chair conformation. The two rings are trans-fused. The pyridine-bound phenyl ring forms dihedral angles of 17.7?(1) and 48.1?(1)°, respectively, with the tosyl and benzyl phenyl rings. The mol-ecular structure is stabilized by an N-H?? inter-action involving the benzyl phenyl ring. In the crystal structure, mol-ecules translated by one unit along the a axis are linked into chains by C-H?? inter-actions involving the benzene ring of the tosyl group.

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