Issue 74, 2005
From the journal:

CrystEngComm

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

David M. Benoit,a   Gregory S. Coumbarides,b   Marco Dingjan,b   Jason Eames,*b   Stephanos Ghilagaberb  and  Majid Motevallib  

* Corresponding authors

a Nachwuchsgruppe Theorie im SFB 569, Albert-Einstein-Allee 11, University of Ulm, D-89081 ULM, Germany

b Department of Chemistry, Queen Mary, University of London, Mile End Road, London, UK
E-mail: j.eames@qmul.ac.uk
Fax: +44-(0)20-7882-7794
Tel: +44-(0)20 7882 5251

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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Article information

DOI
https://doi.org/10.1039/B504667J
Article type
Paper
Submitted
04 Apr 2005
Accepted
29 Jun 2005
First published
06 Jul 2005

CrystEngComm, 2005,7, 454-457

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

D. M. Benoit, G. S. Coumbarides, M. Dingjan, J. Eames, S. Ghilagaber and M. Motevalli, CrystEngComm, 2005, 7, 454 DOI: 10.1039/B504667J

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