(E)-2-[2-(1-Naphthyl)vinyl]-3-tosyl-2,3-dihydro-1,3-benzothiazole

Acta Crystallogr C. 2000 Aug:56 ( Pt 8):992-4. doi: 10.1107/s0108270100006259.

Abstract

The title compound, C(26)H(21)NO(2)S(2), which consists of a benzothiazole skeleton with alpha-naphthylvinyl and tosyl groups at positions 2 and 3, respectively, was prepared by palladium-copper-catalyzed heteroannulation. The E configuration of the molecule about the vinyl C=C bond is established by the benzothiazole-naphthyl C-C-C-C torsion angle of 177.5 (4) degrees. The five-membered heterocyclic ring adopts an envelope conformation with the Csp(3) atom 0.380 (6) A from the C(2)NS plane. The two S-C [1.751 (4) and 1.838 (4) A] and two N-C [1.426 (5) and 1.482 (5) A] bond lengths in the thiazole ring differ significantly.

MeSH terms

  • Benzothiazoles
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Thiazoles / chemistry*
  • Tosyl Compounds / chemistry*

Substances

  • 2-(2-(1-naphthyl)vinyl)-3-tosyl-2,3-dihydro-1,3-benzothiazole
  • Benzothiazoles
  • Thiazoles
  • Tosyl Compounds