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 Citations (Scopus)

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

Fingerprint

Diketopiperazines
Crystal engineering
3,6-bis(5-chloro-2-piperidyl)-2,5-piperazinedione
Carboxylic Acids
Amides
Tapes
Crystals
Enantiomers
X ray crystallography
X Ray Crystallography
Ladders
Hydrogen Bonding
Hydrogen bonds
Crystalline materials
piperazine

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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

In: Tetrahedron, Vol. 55, No. 50, 10.12.1999, p. 14301-14322.

Research output: Contribution to journalArticle

Williams, Lawrence J. ; Jagadish, B. ; Lansdown, Michael G. ; Carducci, Michael D. ; Mash, Eugene A. / 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. In: Tetrahedron. 1999 ; Vol. 55, No. 50. pp. 14301-14322.
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AU - Carducci, Michael D.

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AB - 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.

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