Organic crystal engineering with 1,4-piperazine-2,5-diones. 7. Crystal packing of piperazinediones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid

Deogratias Ntirampebura, Bhumasamudram Jagadish, Gary S. Nichol, Michael D. Carducci, Alice Dawson, Asha Rajapakshe, Allen G. Oliver, William Clegg, Ross W. Harrington, Larry Layne, Jason I. Margolis, Eugene A Mash

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

1,4-Piperazine-2,5-diones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid were prepared in meso, racemic, and enantiomerically pure forms, crystallized from DMSO or DMF, and the supramolecular organization in the crystals determined by X-ray crystallography. These molecules were designed to bear two strongly dipolar p-nitroanisole groups, aligned in the enantiomeric stereoisomers and opposed in the meso stereoisomer. Consistent with piperazinediones of similar size and shape bearing nonpolar or weakly dipolar arene groups, these compounds engage in R22(8) hydrogen bonding, most often forming one-dimensional tapes. However, the preference for arene perpendicular edge-to-center interactions seen in the former is replaced by a preference for parallel edge-to-center arene interactions. While the dipoles of parallel edge-to-center associated arenes are often opposed, this is not a requirement in the solid state.

Original languageEnglish (US)
Pages (from-to)3257-3270
Number of pages14
JournalCrystal Growth and Design
Volume8
Issue number9
DOIs
StatePublished - Sep 2008

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Bearings (structural)
Diketopiperazines
Crystal engineering
Stereoisomerism
X ray crystallography
Dione
Carboxylic Acids
Carboxylic acids
carboxylic acids
Tapes
Hydrogen bonds
engineering
Crystals
Molecules
Dimethyl Sulfoxide
crystals
bears
tapes
crystallography
interactions

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Organic crystal engineering with 1,4-piperazine-2,5-diones. 7. Crystal packing of piperazinediones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid. / Ntirampebura, Deogratias; Jagadish, Bhumasamudram; Nichol, Gary S.; Carducci, Michael D.; Dawson, Alice; Rajapakshe, Asha; Oliver, Allen G.; Clegg, William; Harrington, Ross W.; Layne, Larry; Margolis, Jason I.; Mash, Eugene A.

In: Crystal Growth and Design, Vol. 8, No. 9, 09.2008, p. 3257-3270.

Research output: Contribution to journalArticle

Ntirampebura, D, Jagadish, B, Nichol, GS, Carducci, MD, Dawson, A, Rajapakshe, A, Oliver, AG, Clegg, W, Harrington, RW, Layne, L, Margolis, JI & Mash, EA 2008, 'Organic crystal engineering with 1,4-piperazine-2,5-diones. 7. Crystal packing of piperazinediones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid', Crystal Growth and Design, vol. 8, no. 9, pp. 3257-3270. https://doi.org/10.1021/cg701240m
Ntirampebura, Deogratias ; Jagadish, Bhumasamudram ; Nichol, Gary S. ; Carducci, Michael D. ; Dawson, Alice ; Rajapakshe, Asha ; Oliver, Allen G. ; Clegg, William ; Harrington, Ross W. ; Layne, Larry ; Margolis, Jason I. ; Mash, Eugene A. / Organic crystal engineering with 1,4-piperazine-2,5-diones. 7. Crystal packing of piperazinediones derived from 2-amino-7-nitro-4-methoxyindan-2- carboxylic acid. In: Crystal Growth and Design. 2008 ; Vol. 8, No. 9. pp. 3257-3270.
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