rac-Methyl (3aR*,4S*,5R*,7aR*)-5,7a-bis(acetyloxy)-3-oxo-2-phenyloctahydro-1H-isoindole-4-carboxylate

Acta Crystallographica Section E. 2013;69(10):o1555-o1555 DOI 10.1107/S1600536813025129


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Journal Title: Acta Crystallographica Section E

ISSN: 1600-5368 (Print)

Publisher: International Union of Crystallography

LCC Subject Category: Science: Chemistry

Country of publisher: United Kingdom

Language of fulltext: English

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Flavien A. A. Toze
Eugeniya V. Nikitina
Vladimir P. Zaytsev
Fedor I. Zubkov
Victor N. Khrustalev


Blind peer review

Editorial Board

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Time From Submission to Publication: 3 weeks


Abstract | Full Text

The title molecule, C20H23NO7, the product of nucleophilic cleavage of the 3a,6-epoxy bridge in 1-oxo-2-phenyloctahydro-3a,6-epoxyisoindole-7-carboxylate, comprises a cis-fused bicyclic system containing a 2-pyrrolidinone ring in an envelope conformation (with the C atom bearing the carboxylate substituent as the flap) and a cyclohexane ring in a chair conformation. The carboxylate substituent occupies the equatorial position, whereas the two acetyloxy substituents are in axial positions. The N atom has a trigonal-planar geometry, the sum of the bond angles being 359.3 (3)°. The dihedral angle between the mean plane of the four planar atoms of the pyrrolidinone ring and the phenyl ring is 25.98 (6)°. In the crystal, molecules are linked into zigzag chains along the c-axis direction by C—H...O hydrogen bonds.