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

Takeshi Oishi, Shun Tsuzaki, Tomoya Sugai, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

1 Citation (Scopus)

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)A. 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 tetrasubstituted C atom of the oxolane ring, deviates from the mean plane of other ring atoms by 0.539(4)A. In the crystal, classical O - H⋯O and N - H⋯O hydrogen bonds link the molecules into a sheet structure enclosing an R 4 4(24) graph-set motif. Weak intermolecular C - H⋯O interactions support the sheet formation.

Original languageEnglish
Pages (from-to)756-759
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
DOIs
Publication statusPublished - 2016 May 1

Fingerprint

Crystal structure
Atoms
crystal structure
rings
seats
atoms
Seats
Conformations
Hydrogen bonds
envelopes
Crystals
Molecules
acetamide
hydrogen bonds
deviation
crystals
molecules
1,4-dioxane
interactions

Keywords

  • 1,3-dioxane
  • bicyclic compound
  • crystal structure
  • hydrogen bond
  • hydroxy group
  • oxolane

ASJC Scopus subject areas

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

Cite this

@article{2a4994d28ff047df8c92a3467f89ef01,
title = "Crystal structure of (+)-N-[(1R,5S,6S,9S)-5-hydroxymethyl-3,3,9-trimethyl-8-oxo-2,4,7-trioxabicyclo[4.3.0]nonan-9-yl]acetamide",
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)A. 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 tetrasubstituted C atom of the oxolane ring, deviates from the mean plane of other ring atoms by 0.539(4)A. In the crystal, classical O - H⋯O and N - H⋯O hydrogen bonds link the molecules into a sheet structure enclosing an R 4 4(24) graph-set motif. Weak intermolecular C - H⋯O interactions support the sheet formation.",
keywords = "1,3-dioxane, bicyclic compound, crystal structure, hydrogen bond, hydroxy group, oxolane",
author = "Takeshi Oishi and Shun Tsuzaki and Tomoya Sugai and Takaaki Satou and Noritaka Chida",
year = "2016",
month = "5",
day = "1",
doi = "10.1107/S2056989016006800",
language = "English",
volume = "72",
pages = "756--759",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structure of (+)-N-[(1R,5S,6S,9S)-5-hydroxymethyl-3,3,9-trimethyl-8-oxo-2,4,7-trioxabicyclo[4.3.0]nonan-9-yl]acetamide

AU - Oishi, Takeshi

AU - Tsuzaki, Shun

AU - Sugai, Tomoya

AU - Satou, Takaaki

AU - Chida, Noritaka

PY - 2016/5/1

Y1 - 2016/5/1

N2 - 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)A. 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 tetrasubstituted C atom of the oxolane ring, deviates from the mean plane of other ring atoms by 0.539(4)A. In the crystal, classical O - H⋯O and N - H⋯O hydrogen bonds link the molecules into a sheet structure enclosing an R 4 4(24) graph-set motif. Weak intermolecular C - H⋯O interactions support the sheet formation.

AB - 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)A. 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 tetrasubstituted C atom of the oxolane ring, deviates from the mean plane of other ring atoms by 0.539(4)A. In the crystal, classical O - H⋯O and N - H⋯O hydrogen bonds link the molecules into a sheet structure enclosing an R 4 4(24) graph-set motif. Weak intermolecular C - H⋯O interactions support the sheet formation.

KW - 1,3-dioxane

KW - bicyclic compound

KW - crystal structure

KW - hydrogen bond

KW - hydroxy group

KW - oxolane

UR - http://www.scopus.com/inward/record.url?scp=84969549225&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84969549225&partnerID=8YFLogxK

U2 - 10.1107/S2056989016006800

DO - 10.1107/S2056989016006800

M3 - Article

AN - SCOPUS:84969549225

VL - 72

SP - 756

EP - 759

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

ER -