Research Article: 1-(Anthracen-1-yl)pyrrolidine-2,5-dione

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Sanaz Khorasani, Manuel A. Fernandes.


In the mol­ecular structure of title compound, C18H13NO2, the succinimide ring is orientated away from the plane of the anthracene moiety by 71.94 (4)°. The crystal structure features three different types of inter­molecular inter­actions, viz. C—H⋯O, C—H⋯π and π–π bonds. Mol­ecules along the b axis stack on each other as a result of π–π inter­actions which have a centroid–centroid distance of 3.6780 (15) Å, while C—H⋯π inter­actions are present between neigbouring stacks. Also, acting between the stacks are the C—H⋯O inter­actions between the aromatic H atoms of the anthracene and the O atoms of the succinimide.

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For studies of regio- and sterio-selectivity of substituted anthracenes in Diels–Alder reactions, see: Singh & Ningombom (2010 ▶); Alston et al. (1979 ▶); Meek et al. (1960 ▶); Kaplan & Conroy (1963 ▶); Verma & Singh (1977 ▶). For a study involving NMR experiments, see: Hubbard et al. (1992 ▶).