Issue 37, 2013

Co-crystallisation through halogen bonding with racemic or enantiopure sulfinamides

Abstract

The structures of the racemic and enantiopure forms of a primary sulfinamide reveal a key structure-defining N–H⋯O[double bond, length as m-dash]S hydrogen bond motif that resembles the ubiquitous N–H⋯O[double bond, length as m-dash]C hydrogen bond motif of central importance in protein structures. The presence of the inherently chiral sulfinamide functional group, in contrast to the planar amide, in the hydrogen bonded chains is notable. Halogen bonding with a chiral oxygen acceptor was demonstrated in the co-crystals of the sulfinamide with 1,4-diiodotetraflurobenzene, which reveal a variety of moderate and weak hydrogen and halogen bonding acting co-operatively to form the overall architecture.

Graphical abstract: Co-crystallisation through halogen bonding with racemic or enantiopure sulfinamides

Supplementary files

Article information

Article type
Paper
Submitted
27 May 2013
Accepted
22 Jul 2013
First published
19 Aug 2013

CrystEngComm, 2013,15, 7571-7575

Co-crystallisation through halogen bonding with racemic or enantiopure sulfinamides

K. S. Eccles, R. E. Morrison, C. A. Daly, G. E. O'Mahony, A. R. Maguire and S. E. Lawrence, CrystEngComm, 2013, 15, 7571 DOI: 10.1039/C3CE40932E

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