Hydrogen‐bonded structures and interaction energies in two forms of the SGLT‐2 inhibitor sotagliflozin. Issue 9 (14th August 2017)

• Record Type: Journal Article
• Authors: Gelbrich, Thomas; Adamer, Verena; Stefinovic, Marijan; Thaler, Andrea; Griesser, Ulrich J.
• Is Part Of: Acta crystallographica. Volume 73:Issue 9(2017)
• Page Start: 718
• Page End: 723
• Publication Date: 2017-08-14
• Subjects: sotagliflozin -- SGLT‐2 inhibitor -- crystal structure -- hydrogen bonding -- topology -- PIXEL -- hydrate -- pharmaceuticals; Crystallography -- Periodicals; Crystals -- Periodicals; 548.3
• DOI: 10.1107/S2053229617011603
• Languages: English
• ISSNs: 2053-2296

Abstract

Abstract : The sotagliflozin molecule exhibits two fundamentally different molecular conformations in form 1 and the monohydrate. Hydrogen‐bonded layer structures are based on interactions involving the –OH groups of the xyloside unit. Abstract : 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, C21 H25 ClO5 S, (I)} and the monohydrate [C21 H25 ClO5 S·H2 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‐connectedsql net and that formed by the water and sotagliflozin molecules of (II) has the topology of a 3, 7‐connected net.