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Hydrogen‐bonded structures and interaction energies in two forms of the SGLT‐2 inhibitor sotagliflozin
Author(s) -
Gelbrich Thomas,
Adamer Verena,
Stefinovic Marijan,
Thaler Andrea,
Griesser Ulrich J.
Publication year - 2017
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229617011603
Subject(s) - hydrogen , chemistry , materials science , organic chemistry
The sotagliflozin molecule exhibits two fundamentally different molecular conformations in form 1 {systematic name: (2 S ,3 R ,4 R ,5 S ,6 R )‐2‐[4‐chloro‐3‐(4‐ethoxybenzyl)phenyl]‐6‐(methylsulfanyl)tetrahydro‐2 H ‐pyran‐3,4,5‐triol, C 21 H 25 ClO 5 S, (I)} and the monohydrate [C 21 H 25 ClO 5 S·H 2 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.