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Issue 15, 2011
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Comparison of the polymorphs and solvates of two analogous fungicides—a case study of the applicability of a supramolecular synthon approach in crystal engineering

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Abstract

The polymorphism and solvate formation of thiophanate-ethyl (TE), a fungicidal active, were investigated by solvent crystallization and compared to a close analogue, thiophanate-methyl (TM). Four polymorphs and seven solvates of TE were found and structurally compared with the previously found two polymorphs and fourteen solvates of TM by analyzing the hydrogen bonding patterns and using fingerprint plots, packing coefficients and lattice energies. TE and TM have the same functional groups that can build identical supramolecular synthons. Despite the strong similarities, the polymorphs and solvates of the two actives show significant differences in hydrogen bonding and packing. The results demonstrate the challenges in using a supramolecular synthon approach, and promote the importance in finding methods to also make use of packing effects and lipophilic interactions in crystal engineering.

Graphical abstract: Comparison of the polymorphs and solvates of two analogous fungicides—a case study of the applicability of a supramolecular synthon approach in crystal engineering

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Publication details

The article was received on 17 Jan 2011, accepted on 03 May 2011 and first published on 08 Jun 2011


Article type: Paper
DOI: 10.1039/C1CE05077J
Citation: CrystEngComm, 2011,13, 4956-4964
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    Comparison of the polymorphs and solvates of two analogous fungicides—a case study of the applicability of a supramolecular synthon approach in crystal engineering

    E. Nauha, A. Ojala, M. Nissinen and H. Saxell, CrystEngComm, 2011, 13, 4956
    DOI: 10.1039/C1CE05077J

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