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Issue 7, 2009
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Co-crystallization experiments of thiocarbamides with bipyridine-type molecules

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Abstract

Co-crystallization experiments conducted between thiocarbamide derivatives, (E)-O-alkyl N-aryl-thiocarbamide, ROC([double bond, length as m-dash]S)N(H)R′, for R = Me, Et and iPr, and R′ = Ph and PhNO2-4, containing a pharmaceutically active chromophorei.e. –C([double bond, length as m-dash]S)–N(H)–, and the bipyridine-type molecules, 4,4′-bipyridine, trans-1,2-bis(4-pyridyl)ethene and 1,2-bis(4-pyridyl)ethane, showed the formation of stable 2 : 1 co-crystals, i.e. {[ROC([double bond, length as m-dash]S)N(H)R′]2(bipyridine-type molecule)}. Novel species were formed by grinding and solvent drop grinding methods, and characterized by powder X-ray diffraction. Five 2 : 1 co-crystals were isolated as single crystals by slow evaporation methods and fully characterized by spectroscopic and X-ray crystallographic methods. Uniformly, trimeric aggregates were formed where each pyridine-nitrogen was connected to an amide-H via a Npyridine⋯H–Namide hydrogen bond. This study shows that the eight-membered {⋯H–N–C[double bond, length as m-dash]S}2 homosynthon found in the parent thiocarbamides is readily disrupted in the presence of bipyridine-type molecules to enable the formation of the stable heterosynthon, {N⋯H–N}.

Graphical abstract: Co-crystallization experiments of thiocarbamides with bipyridine-type molecules

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Publication details

The article was received on 15 Dec 2008, accepted on 23 Feb 2009 and first published on 17 Mar 2009


Article type: Paper
DOI: 10.1039/B822555A
Citation: CrystEngComm, 2009,11, 1352-1361
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    Co-crystallization experiments of thiocarbamides with bipyridine-type molecules

    C. A. Ellis, M. A. Miller, J. Spencer, J. Zukerman-Schpector and E. R. T. Tiekink, CrystEngComm, 2009, 11, 1352
    DOI: 10.1039/B822555A

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