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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)555-558
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume74
DOIs
Publication statusPublished - 2018 Apr 1

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Tapes
Crystal structure
Alkaloids
tapes
crystal structure
rings
Amides
Hydrogen bonds
alkaloids
Hydrogen
amides
Crystals
seats
Molecules
Water
envelopes
hydrogen bonds
deviation
water
crystals

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

Cite this

@article{96a3cd2488cf48568f51780b4d53d62c,
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 Satou and Noritaka Chida",
year = "2018",
month = "4",
day = "1",
doi = "10.1107/S2056989018004425",
language = "English",
volume = "74",
pages = "555--558",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

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 - Satou, Takaaki

AU - Chida, Noritaka

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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U2 - 10.1107/S2056989018004425

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VL - 74

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EP - 558

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

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