Issue 15, 2011

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

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

Supplementary files

Article information

Article type
Paper
Submitted
17 Jan 2011
Accepted
03 May 2011
First published
08 Jun 2011

CrystEngComm, 2011,13, 4956-4964

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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