Crystal structure of 5-(1,3-dithian-2-yl)-2H-1,3-benzodioxole

J Zukerman-Schpector, Ignez Caracelli, Hélio A. Stefani, Olga Gozhina, Edward R T Tiekink, W. T A Harrison (Editor)

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Abstract

In the title compound, C11H12O2S2, two independent but virtually superimposable molecules, A and B, comprise the asymmetric unit. In each molecule, the 1,3-dithiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the plane through the remaining four atoms. The substituted benzene ring occupies an equatorial position in each case and forms dihedral angles of 85.62 (9) (molecule A) and 85.69 (8)° (molecule B) with the least-squares plane through the 1,3-dithiane ring. The difference between the molecules rests in the conformation of the five-membered 1,3-dioxole ring which is an envelope in molecule A (the methylene C atom is the flap) and almost planar in molecule B (r.m.s. deviation = 0.046 Å). In the crystal, molecules of A self-associate into supramolecular zigzag chains (generated by glide symmetry along the c axis) via methylene C - H⋯π interactions. Molecules of B form similar chains. The chains pack with no specific directional intermolecular interactions between them.

Original languageEnglish
Pages (from-to)o167-o168
Number of pages2
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number3
DOIs
Publication statusPublished - 1 Mar 2015

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Crystal structure
crystal structure
Molecules
molecules
rings
methylene
Atoms
Conformations
atoms
1,3-benzodioxole
Dihedral angle
Benzene
seats
dihedral angle
envelopes
benzene
interactions
deviation
Crystals
symmetry

Keywords

  • 1,3-benzodioxole
  • 1,3-dithiane
  • C - H⋯πinteractions
  • Conformation
  • Crystal structure

ASJC Scopus subject areas

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

Cite this

Crystal structure of 5-(1,3-dithian-2-yl)-2H-1,3-benzodioxole. / Zukerman-Schpector, J; Caracelli, Ignez; Stefani, Hélio A.; Gozhina, Olga; Tiekink, Edward R T; Harrison, W. T A (Editor).

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 3, 01.03.2015, p. o167-o168.

Research output: Contribution to journalArticle

Zukerman-Schpector, J ; Caracelli, Ignez ; Stefani, Hélio A. ; Gozhina, Olga ; Tiekink, Edward R T ; Harrison, W. T A (Editor). / Crystal structure of 5-(1,3-dithian-2-yl)-2H-1,3-benzodioxole. In: Acta Crystallographica Section E: Structure Reports Online. 2015 ; Vol. 71, No. 3. pp. o167-o168.
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abstract = "In the title compound, C11H12O2S2, two independent but virtually superimposable molecules, A and B, comprise the asymmetric unit. In each molecule, the 1,3-dithiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the plane through the remaining four atoms. The substituted benzene ring occupies an equatorial position in each case and forms dihedral angles of 85.62 (9) (molecule A) and 85.69 (8)° (molecule B) with the least-squares plane through the 1,3-dithiane ring. The difference between the molecules rests in the conformation of the five-membered 1,3-dioxole ring which is an envelope in molecule A (the methylene C atom is the flap) and almost planar in molecule B (r.m.s. deviation = 0.046 {\AA}). In the crystal, molecules of A self-associate into supramolecular zigzag chains (generated by glide symmetry along the c axis) via methylene C - H⋯π interactions. Molecules of B form similar chains. The chains pack with no specific directional intermolecular interactions between them.",
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N2 - In the title compound, C11H12O2S2, two independent but virtually superimposable molecules, A and B, comprise the asymmetric unit. In each molecule, the 1,3-dithiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the plane through the remaining four atoms. The substituted benzene ring occupies an equatorial position in each case and forms dihedral angles of 85.62 (9) (molecule A) and 85.69 (8)° (molecule B) with the least-squares plane through the 1,3-dithiane ring. The difference between the molecules rests in the conformation of the five-membered 1,3-dioxole ring which is an envelope in molecule A (the methylene C atom is the flap) and almost planar in molecule B (r.m.s. deviation = 0.046 Å). In the crystal, molecules of A self-associate into supramolecular zigzag chains (generated by glide symmetry along the c axis) via methylene C - H⋯π interactions. Molecules of B form similar chains. The chains pack with no specific directional intermolecular interactions between them.

AB - In the title compound, C11H12O2S2, two independent but virtually superimposable molecules, A and B, comprise the asymmetric unit. In each molecule, the 1,3-dithiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the plane through the remaining four atoms. The substituted benzene ring occupies an equatorial position in each case and forms dihedral angles of 85.62 (9) (molecule A) and 85.69 (8)° (molecule B) with the least-squares plane through the 1,3-dithiane ring. The difference between the molecules rests in the conformation of the five-membered 1,3-dioxole ring which is an envelope in molecule A (the methylene C atom is the flap) and almost planar in molecule B (r.m.s. deviation = 0.046 Å). In the crystal, molecules of A self-associate into supramolecular zigzag chains (generated by glide symmetry along the c axis) via methylene C - H⋯π interactions. Molecules of B form similar chains. The chains pack with no specific directional intermolecular interactions between them.

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