The second example of doubly enantiophobic behavior during crystallization: a detailed crystallographic, thermochemical and spectroscopic study. Issue 21 (13th May 2021)

• Record Type: Journal Article
• Authors: Gerasimova, Daria P.; Saifina, Alina F.; Zakharychev, Dmitry V.; Fayzullin, Robert R.; Kurbangalieva, Almira R.; Lodochnikova, Olga A.
• Is Part Of: CrystEngComm. Volume 23:Issue 21(2021)
• Page Start: 3907
• Page End: 3918
• Publication Date: 2021-05-13
• Subjects: Crystals -- Periodicals; Crystal growth -- Periodicals; Crystallography -- Periodicals; Cristaux -- Périodiques; Cristaux -- Croissance -- Périodiques; Cristallographie -- Périodiques; 548
• DOI: 10.1039/d1ce00227a
• Languages: English
• ISSNs: 1466-8033

Abstract

Abstract : The formation of two racemic conglomerates with different crystal structures was found. Abstract : Herein we have found a second example of doubly enantiophobic behavior during the crystallization of rac -1-benzyl-3-chloro-4-[(4-chlorophenyl)sulfanyl]-5-hydroxy-1, 5-dihydro-2 H -pyrrol-2-one, i.e., the formation of two conglomerates with different crystal structures in the absence of any racemic compounds. In both polymorphic modifications, the main supramolecular motif is appeared to be a hydrogen-bonded chain or helix of different symmetry, which is related to an α-hydroxyamide chain synthon. Additional crosslinking of the homochiral chains in the crystals of both crystalline forms, which is realized through weak, noncovalent interactions, can be a probable reason for the reproducibility and stability of the α-hydroxyamide chain synthon and polymorphic diversity registered. It was shown that each of the conglomerates is thermodynamically stable in certain temperature ranges. For the first time, a binary phase diagram for the chiral system complicated by an enantiotropic phase transition is reconstructed based on experimental data, which is characterized by the presence of a thermodynamic stability permutation line between the two racemic conglomerates.