Structural similarities and diversity in a series of crystalline solids composed of 2-aminopyridines and glutaric acid

Draguta, Sergiu; Fonarı, Marina S.; Bejagam, Shabari Nath; Storms, Kathryn; Lindline, Jennifer; Timofeeva, Tatiana V.

doi:10.1007/s11224-016-0781-2

Cited by 10 publications

(14 citation statements)

References 57 publications

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“…Despite much effort, only two co-crystals with odd-chain carboxylic acids were obtained. The difficulty of growing crystals with odd-chain carboxylic acids has been previously noted [ 22 , 23 ].…”

Section: Resultsmentioning

confidence: 99%

“…Despite much effort, only two co-crystals with odd-chain carboxy were obtained. The difficulty of growing crystals with odd-chain carboxylic acids h previously noted [22,23]. The resultant solids that showed co-crystal formation were dissol solvents to obtain crystals of diffraction quality; see Table 2 for details crystals that were obtained, 15 produced crystals suitable for single-cry tion (SCXRD).…”

Section: Resultsmentioning

confidence: 99%

“…Despite much effort, only two co-c were obtained. The difficulty of growing crystals w previously noted [22,23].…”

Section: Pyr-imentioning

confidence: 99%

“…ant solids that showed co-crystal formation were dissolved in a variety of ain crystals of diffraction quality; see Table 2 for details. Out of the 47 core obtained, 15 produced crystals suitable for single-crystal X-ray diffrac-Despite much effort, only two co-crystals with odd-chain carboxylic acids The difficulty of growing crystals with odd-chain carboxylic acids has been d [22,23].…”

Section: Pyr-imentioning

confidence: 99%

“…Despite much effort, were obtained. The difficulty of grow previously noted [22,23]. Six co-crystals of 3Pyr-X targets suitable for SCXRD were successfully grown.…”

Section: Code Solventmentioning

confidence: 99%

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The Impact of Halogen Substituents on the Synthesis and Structure of Co-Crystals of Pyridine Amides

2021

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Strategies for co-crystal synthesis tend to employ either hydrogen- or halogen-bonds between different molecules. However, when both interactions are present, the structural influence that they may exert on the resulting assembly is difficult to predict a priori. To shed some light on this supramolecular challenge, we attempted to co-crystallize ten aliphatic dicarboxylic acids (co-formers) with three groups of target molecules; N-(pyridin-2-yl)picolinamides (2Pyr-X), N-(pyridin-2-yl)nicotinamides (3Pyr-X), N-(pyridin-2-yl)isonicotinamides (4Pyr-X); X=Cl/ Br/ I. The structural outcomes were compared with co-crystals prepared from the non-halogenated targets. As expected, none of the reactions with 2Pyr-X produced co-crystals due to the presence of a very stable intramolecular N-H···N hydrogen bond. In the 3Pyr series, all six structures obtained showed the same synthons, –COOH···N(py) and –COOH···N(py)-NH, that were found in the non-halogenated parent 3Pyr and were additionally accompanied by structure directing X···O(OH) interactions (X=Br/I). The co-crystals of the unhalogenated parent 4Pyr co-crystals assembled via intermolecular –COOH···N(py) and –COOH···N(py)-NH synthons. Three of the analogues 4Pyr-X co-crystals displayed only COOH···N(py) and –COOH···N(py)-NH interactions. The three co-crystals of 4Pyr-X with fumaric acid (for which no analogues structures with 4Pyr are known) formed –COOH···N(py)-NH and –NH···O=C hydrogen bonds and showed no structure-directing halogen bonds. In three co-crystals of 4Pyr-I in which –COOH···N(py)-NH hydrogen bond was present, a halogen-bond based –I···N(py) synthon replaced the –COOH···N(py) motif observed in the parent structures. The structural influence of the halogen atoms increased in the order of Cl < Br < I, as the size of σ-holes increased. Finally, it is noteworthy that isostructurality among structures of the homomeric targets was not translated to structural similarities between their respective co-crystals.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Despite much effort, only two co-c were obtained. The difficulty of growing crystals w previously noted [22,23].…”

Section: Pyr-imentioning

confidence: 99%

Section: Pyr-imentioning

confidence: 99%

“…Despite much effort, were obtained. The difficulty of grow previously noted [22,23]. Six co-crystals of 3Pyr-X targets suitable for SCXRD were successfully grown.…”

Section: Code Solventmentioning

confidence: 99%

See 3 more Smart Citations