2011
DOI: 10.1039/c1ce05077j
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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

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 ident… Show more

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Cited by 22 publications
(22 citation statements)
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“…This covers, among other domains, the pharmaceutical [3,4], agrochemical [5,6] or high-energy industries [6][7][8]. Not all multicomponent solids are classified as cocrystals [9] since at least two criterions must be met [9][10][11][12][13].…”
Section: Introductionmentioning
confidence: 99%
“…This covers, among other domains, the pharmaceutical [3,4], agrochemical [5,6] or high-energy industries [6][7][8]. Not all multicomponent solids are classified as cocrystals [9] since at least two criterions must be met [9][10][11][12][13].…”
Section: Introductionmentioning
confidence: 99%
“…In 35 practice, however, packing in crystals is influenced by an intricate combination of close packing incentives, hydrogen bonding and other interactions and therefore there is as yet no reliable way to design co-crystals. Previously, we have been investigating the polymorphism and 40 versatile solvate formation of two agrochemical actives, thiophanate-methyl (TM) 10 and thiophanate-ethyl (TE) 11 (Scheme 1), and decided now to examine co-crystallization with common co-crystal formers, namely 4,4'-bipyridine (44bp) [12][13][14][15][16][17] and 2,2'-bipyridine (22bp) 18 (Scheme 1) as pyridine solvates of TM and 45 TE are also known. Due to the success with the first bipyridines, crystallizations with the similar 1,2-bis(4-pyridyl)ethane (44bpe) (Scheme 1) were also attempted.…”
Section: Introductionmentioning
confidence: 99%
“…Co-crystal design using the pyridine-amine synthon works well for TE, even though it has other functionalities, which could hinder formation of the desired synthon. The packing of the biphenyl co-crystal, however, could not be predicted even though the shape of the molecule is very similar to 2,2'-bipyridine, for which TE builds a packing arrangement containing channels of guest also seen in a number of isomorphic solvates [3]. If no strong hydrogen bonding, like the pyridine amine synthon, to a guest is formed, TE builds chains connected via a R2,2(8) motif of two N-H···S=C hydrogen bonds.…”
Section: Discussionmentioning
confidence: 99%
“…The structures exhibit a complicated array of single and bifurcated hydrogen bonds (Fig. 1), unlike in the other TE structures [3,5], where a pairing of two donors and acceptors is often seen. The two N-H hydrogen atoms that participate in a S(6) intramolecular motif [12] are not further hydrogen bonded.…”
Section: Hydrogen Bonded Co-crystalsmentioning
confidence: 99%
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