Received 29 July 2013
aDepartment of Chemistry, University of Douala, Faculty of Sciences, PO Box 24157, Douala, Republic of , Cameroon,bOrganic Chemistry Department, Peoples' Friendship University of Russia, Miklukho-Maklaya St. 6, Moscow, 117198, Russian Federation, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
Correspondence e-mail: email@example.com
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-HO hydrogen bonds.
For the synthesis of 3a,6-epoxyisoindoles by intramolecular Diels-Alder reactions of furan, see: Vogel et al. (1999); Zubkov et al. (2005). For the synthesis of 2-phenyloctahydroisoindoles and their analogues, see: Balthaser et al. (2011); Zubkov et al. (2011). For related compounds, see: Zubkov et al. (2009, 2012); Claeys et al. (2010).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2096 ).
The authors are grateful to the Russian Foundation for Basic Research for financial support of this work (grant No. 12-03-31088-a).
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