C–H?O Hydrogen bonding induced conformation of (S,S)-1,3-benzenedisulfonyl bis[(4S)-4-(ethyl ester)-oxazolidin-2-one]

CrystEngComm Pub Date: 2005-07-06 DOI: 10.1039/B504667J

Abstract

The conformational arrangement of (S,S)-1,3-benzenedisulfonyl bis[(4S)-4-(ethyl ester)-oxazolidin-2-one] was examined by X-ray crystallography. This revealed an unusual conformational arrangement held together by an internal C–H?O[double bond, length as m-dash]C hydrogen bond. Computational modelling has revealed the native conformer to be 16.94 kJ mol?1 more stable than an open conformation.

Graphical abstract: C–H?O Hydrogen bonding induced conformation of (S,S)-1,3-benzenedisulfonyl bis[(4S)-4-(ethyl ester)-oxazolidin-2-one]
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