Hydrogen-bonded structures and interaction energies in two forms of the SGLT-2 inhibitor sotagliflozin

The sotagliflozin molecule exhibits two fundamentally different molecular conformations in form 1 {systematic name: (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2H-pyran-3,4,5-triol, C H ClO S, (I)} and the monohydrate [C H ClO S·H O, (II)]. Both crystals displ...

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Published inActa crystallographica. Section C, Crystal structure communications Vol. 73; no. Pt 9; p. 718
Main Authors Gelbrich, Thomas, Adamer, Verena, Stefinovic, Marijan, Thaler, Andrea, Griesser, Ulrich J
Format Journal Article
LanguageEnglish
Published England Wiley Subscription Services, Inc 01.09.2017
Subjects
Chemical bonds
Crystallography
Crystals
Hydrogen
Hydrogen bonding
Hydrogen bonds
Molecules
Query languages
Topology
sotagliflozin
hydrogen bonding
topology
SGLT-2 inhibitor
crystal structure
hydrate
pharmaceuticals
PIXEL
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Summary:The sotagliflozin molecule exhibits two fundamentally different molecular conformations in form 1 {systematic name: (2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2H-pyran-3,4,5-triol, C H ClO S, (I)} and the monohydrate [C H ClO S·H O, (II)]. Both crystals display hydrogen-bonded layers formed by intermolecular interactions which involve the three -OH groups of the xyloside fragment of the molecule. The layer architectures of (I) and (II) contain a non-hydrogen-bonded molecule-molecule interaction along the short crystallographic axis (a axis) whose total PIXEL energy exceeds that of each hydrogen-bonded molecule-molecule pair. The hydrogen-bonded layer of (I) has the topology of the 4-connected sql net and that formed by the water and sotagliflozin molecules of (II) has the topology of a 3,7-connected net.
ISSN:0108-2701
2053-2296
1600-5759
DOI:10.1107/S2053229617011603