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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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
Issue number3
Publication statusPublished - 1 Mar 2015

Bibliographical note

We thank Professor Regina H. A. Santos from IQSC–USP for the X-ray data collection. The Brazilian agencies CNPq (305626/2013-2 to JZS, 306121/2013-2 to IC and 308320/2010-7 to HAS), FAPESP (2012/00424-2 and 2013/21925-2) and CAPES are acknowledged for financial support.


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


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