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

 

Journal Homepage

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

Full-text formats available: PDF, HTML

 

AUTHORS

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

EDITORIAL INFORMATION

Blind peer review

Editorial Board

Instructions for authors

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.