Two isomeric butadiene-N-(acetoxyphenyl)maleimide Diels-Alder adducts: supramolecular structure directed by C-H...X (X = O and pi) hydrogen bonds and perpendicular dipole carbonyl-carbonyl interactions

Acta Crystallogr C. 2006 Mar;62(Pt 3):o125-8. doi: 10.1107/S0108270106002186. Epub 2006 Feb 11.

Abstract

The molecular and supramolecular structures of 2-(1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-2-yl)phenyl acetate, C16-H15NO4, (I), and its para isomer, 4-(1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-2-yl)phenyl acetate, (II), are reported. The torsion angle between the succinimide and benzene rings depends on the position of the acetoxy substitution [89.7 (1) and 61.9 (1) degrees for (I) and (II), respectively]. The twist of the acetoxy group relative to the mean plane of the benzene ring is almost independent of the acetoxy position [66.0 (1) and 70.0 (1) degrees ]. Packing interactions for both compounds include soft C-H...X (X = O and Ph) interactions, forming chains of centrosymmetric dimers and interlinked chains for (I) and (II), respectively. In addition, three perpendicular dipole C=O...C=O interactions contribute to the supramolecular structure of (II).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butadienes / chemistry*
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Maleimides / chemistry*
  • Molecular Structure
  • Spectrophotometry, Infrared

Substances

  • Butadienes
  • Maleimides
  • butadiene-N-(acetoxyphenyl)maleimide