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

Takeshi Oishi; Makoto Yoritate; Takaaki Sato; Noritaka Chida

doi:10.1107/S2056989018004425

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

Takeshi Oishi, Makoto Yoritate, Takaaki Sato, Noritaka Chida

Research output: Contribution to journal › Article › peer-review

Abstract

The title compound, C₁₇ H₂₃ NO₄ ·H₂ O, is an epimer of the natural tetracyclic alkaloid isosaxorumamide which consists of a fused 5-7-5 tricyclic core and a dihydrofuranone substituent. The terminal dihydrofuran 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 molecules 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 interactions into a three-dimensional architecture.

Original language	English
Pages (from-to)	555-558
Number of pages	4
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	74
DOIs	https://doi.org/10.1107/S2056989018004425
Publication status	Published - 2018 Apr 1

Keywords

azepane
crystal structure
fused tricyclic core
hydrogen bond
isosaxorumamide
oxolane
pyrrolidine
tetracyclic compound

ASJC Scopus subject areas

Chemistry(all)
Materials Science(all)
Condensed Matter Physics

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Crystal structure of (-)-(5R,7R,8S,9R,10S)-8-methyl-7-[(5 R)-3-methyl-2-oxooxolan-3-en-5-yl]-1-aza-6-oxatricyclo[8.3.0.0 5,9 ]tridecan-13-one monohydrate. / Oishi, Takeshi; Yoritate, Makoto; Sato, Takaaki et al.
In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 74, 01.04.2018, p. 555-558.

Research output: Contribution to journal › Article › peer-review

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

abstract = "The title compound, C17 H23 NO4 ·H2 O, is an epimer of the natural tetracyclic alkaloid isosaxorumamide which consists of a fused 5-7-5 tricyclic core and a dihydrofuranone substituent. The terminal dihydrofuran ring is essentially planar with a maximum deviation of 0.0273(14){\AA} 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 molecules 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 interactions into a three-dimensional architecture.",

keywords = "azepane, crystal structure, fused tricyclic core, hydrogen bond, isosaxorumamide, oxolane, pyrrolidine, tetracyclic compound",

author = "Takeshi Oishi and Makoto Yoritate and Takaaki Sato and Noritaka Chida",

note = "Funding Information: This research was partially supported by the Keio Gijuku Fukuzawa Memorial Fund for the Advancement of Education and Research. We also thank Professor S. Ohba (Keio University, Japan) for his fruitful advice. Publisher Copyright: {\textcopyright} 2018 Oishi et al.",

year = "2018",

month = apr,

day = "1",

doi = "10.1107/S2056989018004425",

language = "English",

volume = "74",

pages = "555--558",

journal = "Acta Crystallographica Section E: Crystallographic Communications",

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TY - JOUR

T1 - Crystal structure of (-)-(5R,7R,8S,9R,10S)-8-methyl-7-[(5 R)-3-methyl-2-oxooxolan-3-en-5-yl]-1-aza-6-oxatricyclo[8.3.0.0 5,9 ]tridecan-13-one monohydrate

AU - Oishi, Takeshi

AU - Yoritate, Makoto

AU - Sato, Takaaki

AU - Chida, Noritaka

N1 - Funding Information: This research was partially supported by the Keio Gijuku Fukuzawa Memorial Fund for the Advancement of Education and Research. We also thank Professor S. Ohba (Keio University, Japan) for his fruitful advice. Publisher Copyright: © 2018 Oishi et al.

PY - 2018/4/1

Y1 - 2018/4/1

N2 - The title compound, C17 H23 NO4 ·H2 O, is an epimer of the natural tetracyclic alkaloid isosaxorumamide which consists of a fused 5-7-5 tricyclic core and a dihydrofuranone substituent. The terminal dihydrofuran 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 molecules 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 interactions into a three-dimensional architecture.

AB - The title compound, C17 H23 NO4 ·H2 O, is an epimer of the natural tetracyclic alkaloid isosaxorumamide which consists of a fused 5-7-5 tricyclic core and a dihydrofuranone substituent. The terminal dihydrofuran 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 molecules 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 interactions into a three-dimensional architecture.

KW - azepane

KW - crystal structure

KW - fused tricyclic core

KW - hydrogen bond

KW - isosaxorumamide

KW - oxolane

KW - pyrrolidine

KW - tetracyclic compound

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DO - 10.1107/S2056989018004425

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JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

ER -

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

Abstract

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