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Molecular co-crystals of 2-aminothiazole derivatives

Lynch, Daniel E., Nicholls, Laura J., Smith, Graham, Byriel, Karl A., & Kennard, Colin H. L. (1999) Molecular co-crystals of 2-aminothiazole derivatives. Acta Crystallographica. Section B: Structural Science, B55, pp. 758-766.

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Abstract

A series of molecular adducts of 2-aminothiazole derivatives - 2-aminothiazole, 2-amino-2-thiazoline and 2-aminobenzothiazole with the carboxylic-acid-substituted heterocyclics indole-2-carboxylic acid, N-methylpyrrole-2-carboxylic acid and thiophene-2-carboxylic acid - have been prepared and characterized using X-ray powder diffraction and in five cases by single-crystal X-ray diffraction methods. These five compounds are the adducts of 2-amino-2-thiazolium with indole-2-carboxylate [(C3H7N2S)+(C9H6NO2)-], and N-methylpyrrole-2-carboxylate [(C3H7N2S)+-(C6H6NO2)-], 2-aminobenzothiazolium with indole-2-carboxylate [(C7H7N2S)+(C9H6NO2)-], N-methylpyrrole-2-carboxylate [(C7H7N2S)+(C6H6NO2)-] and thiophene-2-carboxylate [(C7H7N2S)+(C5H3O2S)-]. All complexes involve proton transfer, as indicated by IR spectroscopy, while the five crystal structures display similar hydrogen-bonding patterns with the dominant interaction being an graph set dimer association between carboxylate groups and the amine/heterocyclic nitrogen sites. Futhermore, in each case a subsiduary interaction between an amino proton and a carboxylate oxygen completes a linear hydrogen-bonded chain. In addition to this, the indole-2-carboxylate molecules in the adduct structure with 2-amino-2-thiazolium form associated dimers which add to the hydrogen-bonding network.

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ID Code: 13134
Item Type: Journal Article
Keywords: 2, Aminothiazole derivatives, Proton transfer
DOI: 10.1107/S0108768199003146
ISSN: 0108-7681
Divisions: Past > QUT Faculties & Divisions > Faculty of Science and Technology
Copyright Owner: Copyright 1999 International Union of Crystallography
Copyright Statement: Reproduced in accordance with the copyright policy of the publisher.
Deposited On: 25 Mar 2008
Last Modified: 10 Aug 2011 23:26

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