An unusual syn conformation of 5-formyluracil stabilized by supramolecular interactions

Acta Crystallogr C. 2007 Nov;63(Pt 11):o650-4. doi: 10.1107/S0108270107045659. Epub 2007 Oct 13.

Abstract

The asymmetric unit of the amino-oxo tautomer of 5-formyluracil (systematic name: 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde), C(5)H(4)N(2)O(3), comprises one planar amino-oxo tautomer, as every atom in the structure lies on a crystallographic mirror plane. At variance with all the previously reported small-molecule crystal structures containing the 5-formyluracil residue, the formyl substituent in the title compound exhibits an unusual syn conformation. The molecules are linked into planar sheets parallel to the bc plane by a combination of six N-H...O and C-H...O hydrogen bonds. Four of the hydrogen bonds are utilized to stabilize the formyl group in the syn conformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Molecular Conformation
  • Mutagens / chemistry*
  • Stereoisomerism
  • Uracil / analogs & derivatives*
  • Uracil / chemistry

Substances

  • Mutagens
  • 5-formyluracil
  • Uracil