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Synthesis, crystallisation and thermodynamics of two polymorphs of a new derivative of meglumine: 1-(2,2,3-trimethyl-1,3-oxazolidin-5-yl)-butane-1,2,3,4-tetrol

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Abstract

A new compound, 1-(2,2,3-trimethyl-1,3-oxazolidin-5-yl)-butane-1,2,3,4-tetrol, has been discovered, described, and its crystal polymorphism investigated. The crystal structures of two polymorphs have been solved with single-crystal X-ray diffraction. The molecule is chiral with four stereo centers, and both polymorphs crystallise in the non-centrosymmetric orthorhombic, chiral P212121 space group, with one molecule in the asymmetric unit. In both structures the molecules are arranged three dimensionally in an interlocked manner, stabilized by strong O–H⋯O and weaker C–H⋯O and π⋯π interactions. The polymorphs have been characterized by X-ray powder diffraction (XRPD) and infrared spectroscopy (IR). The thermodynamic stability relationship between the polymorphs from 280 K up to the melting points has been quantitatively determined by differential scanning calorimetry (DSC), through measurement of melting points, heats of fusion, and heat capacities of the solid phases and the supercooled melt. It is established that the relationship is most likely monotropic, with one polymorph (FI) stable throughout the entire evaluated temperature range. The stability relationship at room temperature has been confirmed by a slurry conversion experiment.

Graphical abstract: Synthesis, crystallisation and thermodynamics of two polymorphs of a new derivative of meglumine: 1-(2,2,3-trimethyl-1,3-oxazolidin-5-yl)-butane-1,2,3,4-tetrol

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Publication details

The article was received on 17 Jun 2017, accepted on 30 Nov 2017 and first published on 01 Dec 2017


Article type: Paper
DOI: 10.1039/C7CE01135K
Citation: CrystEngComm, 2018, Advance Article
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    Synthesis, crystallisation and thermodynamics of two polymorphs of a new derivative of meglumine: 1-(2,2,3-trimethyl-1,3-oxazolidin-5-yl)-butane-1,2,3,4-tetrol

    M. Svärd, G. R. Krishna and Å. C. Rasmuson, CrystEngComm, 2018, Advance Article , DOI: 10.1039/C7CE01135K

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