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Issue 48, 2017
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Structural aspects of partial solid solution formation: two crystalline modifications of a chiral derivative of 1,5-dihydro-2H-pyrrol-2-one under consideration

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Abstract

The purposeful change of crystallization conditions for rac-3-chloro-5-hydroxy-1-(4-methylbenzyl)-4-[(4-methylphenyl)sulfanyl]-1,5-dihydro-2H-pyrrol-2-one 1 leads to two different crystal modifications, namely, a racemic compound in the triclinic space group P[1 with combining macron] with Z′ = 1 (α-1) and a partial solid solution based on a racemic compound in the monoclinic space group P21 with Z′ = 4 (β-1). The first modification, α-1, is characterized by a higher density of the molecular packing in the crystal, while the second one, β-1, by a stronger system of hydrogen bonds and the presence of positional and substitutional disorder simultaneously. The analysis of the crystal structure of modifications α and β allowed us to define some structural aspects of the partial solid solution formation. Namely, the tendency to build a stronger hydrogen bond system enables the solution of enantiomers of 1 to be formed in the crystalline phase, whereas the propensity of the molecules to adopt a more favorable transoid conformation limits the solubility of the minor enantiomer.

Graphical abstract: Structural aspects of partial solid solution formation: two crystalline modifications of a chiral derivative of 1,5-dihydro-2H-pyrrol-2-one under consideration

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Publication details

The article was received on 27 Sep 2017, accepted on 15 Nov 2017 and first published on 16 Nov 2017


Article type: Paper
DOI: 10.1039/C7CE01717K
Citation: CrystEngComm, 2017,19, 7277-7286
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    Structural aspects of partial solid solution formation: two crystalline modifications of a chiral derivative of 1,5-dihydro-2H-pyrrol-2-one under consideration

    O. A. Lodochnikova, L. S. Kosolapova, A. F. Saifina, A. T. Gubaidullin, R. R. Fayzullin, A. R. Khamatgalimov, I. A. Litvinov and A. R. Kurbangalieva, CrystEngComm, 2017, 19, 7277
    DOI: 10.1039/C7CE01717K

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