Issue 48, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Sep 2017
Accepted
15 Nov 2017
First published
16 Nov 2017
This article is Open Access
Creative Commons BY-NC license

CrystEngComm, 2017,19, 7277-7286

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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