Crystal structure of (+)-N-[(1R,5S,6S,9S)-5-hydroxy-methyl-3,3,9-trimethyl-8-oxo-2,4,7-trioxabi-cyclo-[4.3.0]nonan-9-yl]acetamide

Takeshi Oishi; Shun Tsuzaki; Tomoya Sugai; Takaaki Sato; Noritaka Chida

doi:10.1107/S2056989016006800

Crystal structure of (+)-N-[(1R,5S,6S,9S)-5-hydroxy-methyl-3,3,9-trimethyl-8-oxo-2,4,7-trioxabi-cyclo-[4.3.0]nonan-9-yl]acetamide

Acta Crystallogr E Crystallogr Commun. 2016 Apr 29;72(Pt 5):756-9. doi: 10.1107/S2056989016006800. eCollection 2016 May 1.

Authors

Takeshi Oishi¹, Shun Tsuzaki², Tomoya Sugai², Takaaki Sato², Noritaka Chida²

Affiliations

¹ School of Medicine, Keio University, Hiyoshi 4-1-1, Kohoku-ku, Yokohama 223-8521, Japan.
² Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yokohama 223-8522, Japan.

Abstract

In the title compound, C12H19NO6, the six-membered 1,3-dioxane ring adopts a chair-like conformation. The seat of this chair, containing two O atoms, is essentially planar, with a maximum deviation of 0.0021 (12) Å. The five-membered oxolane ring cis-fused to the 1,3-dioxane ring adopts an envelope form. The bridgehead C atom at the flap, which is bonded to the tetra-substituted C atom of the oxolane ring, deviates from the mean plane of other ring atoms by 0.539 (4) Å. In the crystal, classical O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a sheet structure enclosing an R 4 (4)(24) graph-set motif. Weak inter-molecular C-H⋯O inter-actions support the sheet formation.

Keywords: 1,3-dioxane; bicyclic compound; crystal structure; hydrogen bond; hydroxy group; oxolane.