(Z)-3-(1H-Indol-3-yl)-2-(3-thienyl)acrylonitrile and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]-2-(3-thienyl)acrylonitrile

Acta Crystallogr C. 2005 Feb;61(Pt 2):o78-80. doi: 10.1107/S0108270104032925. Epub 2005 Jan 15.

Abstract

(Z)-3-(1H-Indol-3-yl)-2-(3-thienyl)acrylonitrile, C15H10N2S, (I), and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]-2-(3-thienyl)acrylonitrile, C26H24N2S, (II), were prepared by base-catalyzed reactions of the corresponding indole-3-carboxaldehyde with thiophene-3-acetonitrile. 1H/13C NMR spectral data and X-ray crystal structures of compounds (I) and (II) are presented. The olefinic bond connecting the indole and thiophene moieties has Z geometry in both cases, and the molecules crystallize in space groups P2(1)/c and C2/c for (I) and (II), respectively. Slight thienyl ring-flip disorder (ca 5.6%) was observed and modeled for (I).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acrylonitrile / analogs & derivatives*
  • Acrylonitrile / chemistry
  • Benzyl Compounds / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Indoles / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Thiophenes / chemistry*

Substances

  • Benzyl Compounds
  • Indoles
  • Thiophenes
  • Acrylonitrile