4-Imino-1,3-diazabicyclo[3.1.0]hexan-2-one

Philip J. Kuehl, Michael D. Carducci, Paul B Myrdal

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The title compound, also known as imexon, C4H5N 3O, is an iminopyrrolidone that, due to its selective growth inhibitory effect against multiple myeloma, has been under investigation as an anticancer agent since the 1970s. Crystals of the title compound were grown from absolute ethanol saturated with imexon at 296 K, by slow evaporation. Under these conditions, imexon crystallizes as plates with well developed (100) faces. The crystals readily twin by a twofold rotation about the a axis. When crystallized via rapid evaporation of solvent, the resulting powder has a slightly larger unit cell. Simulation of the powder pattern using the atomic parameters and the larger powder cell agree well with measured powder patterns but indicate some preferred orientation towards the (100) plane. The anticancer molecule crystallizes as a zwitterion, with the imino N atom doubly protonated. Each molecule makes four hydrogen bonds which form continuous tapes of molecules along [010].

Original languageEnglish (US)
JournalActa Crystallographica Section E: Structure Reports Online
Volume62
Issue number9
DOIs
StatePublished - Sep 2006

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Powders
Molecules
Evaporation
evaporation
molecules
Crystals
zwitterions
cells
Multiple Myeloma
Antineoplastic Agents
Tapes
tapes
crystals
Hydrogen
Hydrogen bonds
Ethanol
ethyl alcohol
hydrogen bonds
Atoms
4-imino-1,3-diazabicyclo(3.1.0)hexan-2-one

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Structural Biology

Cite this

4-Imino-1,3-diazabicyclo[3.1.0]hexan-2-one. / Kuehl, Philip J.; Carducci, Michael D.; Myrdal, Paul B.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 62, No. 9, 09.2006.

Research output: Contribution to journalArticle

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