Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 10 (October 2013)

organic compounds

Acta Cryst. (2013). E69, o1555    [ doi:10.1107/S1600536813025129 ]

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

F. A. A. Toze, E. V. Nikitina, V. P. Zaytsev, F. I. Zubkov and V. N. Khrustalev

Abstract: 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.

CCDC reference: 960159

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