Crystal structure of (-)-(r,e)-3-(1,3-benzodioxol-5-yl)-5-[(4s,5r)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-n,n-dimethylpent-4-enamide

Takeshi Oishi, Koki Ishii, Mizuki Ishibashi, Takaaki Satou, Noritaka Chida

Research output: Contribution to journalArticle

Abstract

In the title compound, C20H27NO6, the amide moiety is essentially planar, with a maximum deviation of 0.073(3)Å, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564(7)Å. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215(7)Å. The C-C=C-C olefin moiety is essentially planar and makes a dihedral angle of 87.1(3)° with the benzene ring. An intramolecular O-H O hydrogen bond supports the molecular conformation, enclosing an S(11) graph-set motif. In the crystal, intermolecular C-H O hydrogen bonding links the molecules into a tape running along the b axis. Furthermore, other weak C-H;O hydrogen bonds and a C-Hπ interaction connect the tapes into a sheet structure parallel to (100).

Original languageEnglish
Pages (from-to)825-828
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume74
DOIs
Publication statusPublished - 2018 Jan 1

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Crystal structure
Atoms
crystal structure
Hydrogen bonds
rings
atoms
Alkenes
Benzene
Tapes
tapes
alkenes
Olefins
envelopes
benzene
hydrogen bonds
Dihedral angle
Amides
amides
Conformations
dihedral angle

Keywords

  • 1, 3-benzodioxole
  • 1, 3-dioxolane
  • Amide
  • Crystal structure
  • Hydrogen bond
  • Hydroxy group

ASJC Scopus subject areas

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

Cite this

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title = "Crystal structure of (-)-(r,e)-3-(1,3-benzodioxol-5-yl)-5-[(4s,5r)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-n,n-dimethylpent-4-enamide",
abstract = "In the title compound, C20H27NO6, the amide moiety is essentially planar, with a maximum deviation of 0.073(3){\AA}, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564(7){\AA}. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215(7){\AA}. The C-C=C-C olefin moiety is essentially planar and makes a dihedral angle of 87.1(3)° with the benzene ring. An intramolecular O-H O hydrogen bond supports the molecular conformation, enclosing an S(11) graph-set motif. In the crystal, intermolecular C-H O hydrogen bonding links the molecules into a tape running along the b axis. Furthermore, other weak C-H;O hydrogen bonds and a C-Hπ interaction connect the tapes into a sheet structure parallel to (100).",
keywords = "1, 3-benzodioxole, 1, 3-dioxolane, Amide, Crystal structure, Hydrogen bond, Hydroxy group",
author = "Takeshi Oishi and Koki Ishii and Mizuki Ishibashi and Takaaki Satou and Noritaka Chida",
year = "2018",
month = "1",
day = "1",
doi = "10.1107/S2056989018007132",
language = "English",
volume = "74",
pages = "825--828",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",

}

TY - JOUR

T1 - Crystal structure of (-)-(r,e)-3-(1,3-benzodioxol-5-yl)-5-[(4s,5r)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-n,n-dimethylpent-4-enamide

AU - Oishi, Takeshi

AU - Ishii, Koki

AU - Ishibashi, Mizuki

AU - Satou, Takaaki

AU - Chida, Noritaka

PY - 2018/1/1

Y1 - 2018/1/1

N2 - In the title compound, C20H27NO6, the amide moiety is essentially planar, with a maximum deviation of 0.073(3)Å, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564(7)Å. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215(7)Å. The C-C=C-C olefin moiety is essentially planar and makes a dihedral angle of 87.1(3)° with the benzene ring. An intramolecular O-H O hydrogen bond supports the molecular conformation, enclosing an S(11) graph-set motif. In the crystal, intermolecular C-H O hydrogen bonding links the molecules into a tape running along the b axis. Furthermore, other weak C-H;O hydrogen bonds and a C-Hπ interaction connect the tapes into a sheet structure parallel to (100).

AB - In the title compound, C20H27NO6, the amide moiety is essentially planar, with a maximum deviation of 0.073(3)Å, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564(7)Å. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215(7)Å. The C-C=C-C olefin moiety is essentially planar and makes a dihedral angle of 87.1(3)° with the benzene ring. An intramolecular O-H O hydrogen bond supports the molecular conformation, enclosing an S(11) graph-set motif. In the crystal, intermolecular C-H O hydrogen bonding links the molecules into a tape running along the b axis. Furthermore, other weak C-H;O hydrogen bonds and a C-Hπ interaction connect the tapes into a sheet structure parallel to (100).

KW - 1, 3-benzodioxole

KW - 1, 3-dioxolane

KW - Amide

KW - Crystal structure

KW - Hydrogen bond

KW - Hydroxy group

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