Hydrogen-bonded dimers in 3-amino-4-anilino-1H-isochromen-1-one and a hydrogen-bonded sheet in 3-amino-4-[methyl(phenyl)amino]-1H-isochromen-1-one

Acta Crystallogr C. 2013 Jul;69(Pt 7):770-3. doi: 10.1107/S0108270113014777. Epub 2013 Jun 8.

Abstract

The molecules of 3-amino-4-anilino-1H-isochromen-1-one, C15H12N2O2, (I), and 3-amino-4-[methyl(phenyl)amino]-1H-isochromen-1-one, C16H14N2O2, (II), adopt very similar conformations, with the substituted amino group PhNR, where R = H in (I) and R = Me in (II), almost orthogonal to the adjacent heterocyclic ring. The molecules of (I) are linked into cyclic centrosymmetric dimers by pairs of N-H···O hydrogen bonds, while those of (II) are linked into complex sheets by a combination of one three-centre N-H···(O)2 hydrogen bond, one two-centre C-H···O hydrogen bond and two C-H···π(arene) hydrogen bonds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid / chemistry*
  • Aniline Compounds / chemistry*
  • Benzoic Acid / chemistry*
  • Crystallography, X-Ray
  • Dimerization
  • Hydrogen Bonding
  • Isocoumarins / chemistry*
  • Methanol / chemistry
  • Molecular Structure

Substances

  • 3-amino-4-(methyl(phenyl)amino)-1H-isochromen-1-one
  • 3-amino-4-anilino-1H-isochromen-1-one
  • Aniline Compounds
  • Isocoumarins
  • Benzoic Acid
  • Acetic Acid
  • aniline
  • methylaniline
  • Methanol