Organic crystal engineering with piperazine-2,5-diones. 2. Crystal packing of weakly dipolar piperazinediones derived from 2-amino-4-bromo-7- methoxyindan-2-carboxylic acid

Lawrence J. Williams, B. Jagadish, Michael G. Lansdown, Michael D. Carducci, Eugene A. Mash

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

Piperazine-2,5-diones with the potential to manifest three chemically distinct and linearly independent intermolecular interactions were synthesized from the enantiomers of 2-amino-4-bromo-7-methoxyindan-2- carboxylic acid. Samples of enantiomerically pure, racemic, and meso piperazinediones were characterized in the solid state by X-ray crystallography. 'Ladder-like' intermolecular amide-to-amide hydrogen bonding interactions were observed in each case, establishing tape structures parallel to one crystallographic axis. The observed tape morphologies and crystal packing closely resemble that previously observed for a topographically similar tetramethoxy-piperazinedione. The results obtained demonstrate that the weak dipoles associated with the p-bromoanisole moiety play no role in determining order in the crystalline state.

Original languageEnglish (US)
Pages (from-to)14301-14322
Number of pages22
JournalTetrahedron
Volume55
Issue number50
DOIs
StatePublished - Dec 10 1999

Keywords

  • Amino acids and derivatives
  • Indanes
  • Piperazinones
  • X-Ray crystal structures

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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