Three polymorphs of 3-(3-phenyl-1<i>H</i>-1,2,4-triazol-5-yl)-2<i>H</i>-1-benzopyran-2-one formed from different solvents

Shishkina, Svitlana V.; Konovalova, Irina S.; Trostianko, Pavlo V.; Geleverya, Anna O.; Kovalenko, Sergiy M.; Bunyatyan, N. D.

doi:10.1107/s2053229619006405

Cited by 3 publications

(5 citation statements)

References 42 publications

(31 reference statements)

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“…The centrosymmetric triclinic (denoted 1t) and noncentrosymmetric orthorhombic crystals (denoted 1r) were found to be in an equal ratio. The concomitant crystallization of centrosymmetric and noncentrosymmetric polymorphs is a rare phenomenon and has been studied with respect to organic nonlinear optical (NLO) materials (Timofeeva et al, 2000(Timofeeva et al, , 2003Jha et al, 2018) and 3-(3-phenyl-1H-1,2,4-triazol-5yl)-2H-1-benzopyran-2-one (Shishkina et al, 2019).…”

Section: Crystallizationmentioning

confidence: 99%

Concomitant polymorphic forms of 3-cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole

Shishkina

Konovalova

Karpina

et al. 2020

Acta Crystallogr C Struct Chem

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The dipharmacophore compound 3-cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole, C10H11N5O, was studied on the assumption of its potential biological activity. Two concomitant polymorphs were obtained on crystallization from isopropanol solution and these were thoroughly studied. Identical conformations of the molecules are found in both structures despite the low difference in energy between the four possible conformers. The two polymorphs differ crucially with respect to their crystal structures. A centrosymmetric dimer formed due to both stacking interactions of the `head-to-tail' type and N—H...N(π) hydrogen bonds is the building unit in the triclinic structure. The dimeric building units form an isotropic packing. In the orthorhombic polymorphic structure, the molecules form stacking interactions of the `head-to-head' type, which results in their organization in a column as the primary basic structural motif. The formation of N—H...N(lone pair) hydrogen bonds between two neighbouring columns allows the formation of a double column as the main structural motif. The correct packing motifs in the two polymorphs could not be identified without calculations of the pairwise interaction energies. The triclinic structure has a higher density and a lower (by 0.60 kcal mol−1) lattice energy according to periodic calculations compared to the orthorhombic structure. This allows us to presume that the triclinic form of 3-cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole is the more stable.

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Section: Crystallizationmentioning

confidence: 99%

Concomitant polymorphic forms of 3-cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole

Shishkina

Konovalova

Karpina

et al. 2020

Acta Crystallogr C Struct Chem

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“…The barrier of rotation around the C8-C10 bond was calculated as the difference in energy between the transition state and the more stable equilibrium geometry; this is 5.35 kcal mol À1 for compound 1 and 5.41 kcal mol À1 for compound 2. It is half as much as compared to the barrier of rotation calculated for 3-(5phenyl-4H-1,2,4-triazol-3-yl)-2H-chromen-2-one, where the conformer with the lowest energy is stabilized by an intramolecular N-HÁ Á ÁN hydrogen bond (Shishkina et al, 2019). Thus, the molecules of 1 and 2 are more flexible compared to the earlier studied coumarin-triazolyl derivative due to the absence of strong intramolecular interactions.…”

Section: Resultsmentioning

confidence: 84%

“…The presence of an extended -system creates preconditions for the formation of stacking interactions which is soft enough to provide a shift of the stacked molecules. Such molecules are capable of forming a large number of polymorphic modifications (Shtukenberg et al, 2017;Dolgushin et al, 2016;Shishkina et al, 2019).…”

Section: Resultsmentioning

confidence: 99%

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Polymorphism of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)- and 3-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-ones

et al. 2019

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This study of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one, C 17 H 10 N 2 O 3 , 1, and 3-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-one, C 16 H 9 N 3 O 3 , 2, was performed on the assumption of the potential anticancer activity of the compounds. Three polymorphic structures for 1 and two polymorphic structures for 2 have been studied thoroughly. The strongest intermolecular interaction is stacking of the 'head-to-head' type in all the studied crystals. The polymorphic structures of 1 differ with respect to the intermolecular interactions between stacked columns. Two of the polymorphs have a columnar or double columnar type of crystal organization, while the third polymorphic structure can be classified as columnar-layered. The difference between the two structures of 2 is less pronounced. Both crystals can be considered as having very similar arrangements of neighbouring columns. The formation of polymorphic modifications is caused by a subtle balance of very weak intermolecular interactions and packing differences can be identified only using an analysis based on a study of the pairwise interaction energies.

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“…It is useful to note that crystallization of noncentrosymmetric and centrosymmetric crystals from the same solution is a known phenomenon (Timofeeva et al, 2000(Timofeeva et al, , 2003Jha et al, 2018;Shishkina et al, 2019Shishkina et al, , 2020Constantinides et al, 2020). In many cases, the noncentrosymmetric polymorphic form crystallizes first, while the centrosymmetric form results from slower crystallization.…”

Section: Figurementioning

confidence: 99%

Polymorphism of methyl 4-amino-3-phenylisothiazole-5-carboxylate: an experimental and theoretical study

Shishkina¹,

Konovalova²,

Kovalenko³

et al. 2021

Acta Crystallogr C Struct Chem

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Being a close analogue of amflutizole, methyl 4-amino-3-phenylisothiazole-5-carboxylate (C11H10N2O2S) was assumed to be capable of forming polymorphic structures. Noncentrosymmetric and centrosymmetric polymorphs have been obtained by crystallization from a series of more volatile solvents and from denser tetrachloromethane, respectively. Identical conformations of the molecule are found in both structures. The two polymorphs differ mainly in the intermolecular interactions formed by the amino group and in the type of stacking interactions between the π-systems. The most effective method for revealing packing motifs in structures with intermolecular interactions of different types (hydrogen bonding, stacking, dispersion, etc.) is to study the pairwise interaction energies using quantum chemical calculations. Molecules form a column as the primary basic structural motif due to stacking interactions in both polymorphic structures under study. The character of a column (straight or zigzag) is determined by the orientations of the stacked molecules (in a `head-to-head' or `head-to-tail' manner). Columns bound by intermolecular N—H...O and N—H...N hydrogen bonds form a double column as the main structural motif in the noncentrosymmetric structure. Double columns in the noncentrosymmetric structure and columns in the centrosymmetric structure interact strongly within the ab crystallographic plane, forming a layer as a secondary basic structural motif. The noncentrosymmetric structure has a lower density and a lower (by 0.59 kJ mol−1) lattice energy, calculated using periodic calculations, compared to the centrosymmetric structure.

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Three polymorphs of 3-(3-phenyl-1H-1,2,4-triazol-5-yl)-2H-1-benzopyran-2-one formed from different solvents

Cited by 3 publications

References 42 publications

Concomitant polymorphic forms of 3-cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole

Concomitant polymorphic forms of 3-cyclopropyl-5-(2-hydrazinylpyridin-3-yl)-1,2,4-oxadiazole

Polymorphism of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)- and 3-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-ones

Polymorphism of methyl 4-amino-3-phenylisothiazole-5-carboxylate: an experimental and theoretical study

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