Crystal structure of (-)-(5 R,7 R,8 S,9 R,10 S)-8-methyl-7-[(5 R)-3-methyl-2-oxooxolan-3-en-5-yl]-1-aza-6-oxatri-cyclo-[8.3.0.05,9]tridecan-13-one monohydrate

Takeshi Oishi; Makoto Yoritate; Takaaki Sato; Noritaka Chida

doi:10.1107/S2056989018004425

Crystal structure of (-)-(5 R,7 R,8 S,9 R,10 S)-8-methyl-7-[(5 R)-3-methyl-2-oxooxolan-3-en-5-yl]-1-aza-6-oxatri-cyclo-[8.3.0.0^5,9]tridecan-13-one monohydrate

Acta Crystallogr E Crystallogr Commun. 2018 Mar 27;74(Pt 4):555-558. doi: 10.1107/S2056989018004425. eCollection 2018 Apr 1.

Authors

Takeshi Oishi¹, Makoto Yoritate², 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

The title compound, C₁₇H₂₃NO₄·H₂O, is an epimer of the natural tetra-cyclic alkaloid isosaxorumamide which consists of a fused 5-7-5 tricyclic core and a di-hydro-furan-one substituent. The terminal di-hydro-furan ring is essentially planar with a maximum deviation of 0.0273 (14) Å from the mean plane and oxolane, azepane and pyrrolidine rings in the tricyclic ring system adopt twist, twist-chair and envelope forms, respectively. In the crystal, the amide and water mol-ecules are linked by O-H⋯O hydrogen bonds, forming a tape structure running along the b-axis direction. The tapes are further connected by C-H⋯O inter-actions into a three-dimensional architecture.

Keywords: azepane; crystal structure; fused tricyclic core; hydrogen bond; isosaxorumamide; oxolane; pyrrolidine; tetracyclic compound.