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Issue 42, 2013
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The competition between halogen bonds (Br⋯O) and C–H⋯O hydrogen bonds: the structure of the acetone–bromine complex revisited

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Abstract

A combination of single-crystal X-ray (at 110 and 200 K) and high-resolution neutron powder diffraction (110 K only) using perdeuterated samples has been used to re-determine the crystal structure of the well-known acetone–Br2 complex. The results indicate a significant interaction between the carbonyl oxygen and the nearest Br atom leading to a marked elongation of the molecular Br–Br bond. In the earlier widely cited crystal structure, no such elongation was reported. Furthermore, the new structure indicates the presence of additional weaker C–H⋯O and C–H⋯Br interactions. In this simple complex, in which the halogen bonding is strong compared to the hydrogen bonding (C–H⋯O), the former interaction is found to occur close (~12°) to the plane of the carbonyl group, with the C–H⋯Br complementing the stronger halogen bond.

Graphical abstract: The competition between halogen bonds (Br⋯O) and C–H⋯O hydrogen bonds: the structure of the acetone–bromine complex revisited

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Supplementary files

Article information


Submitted
25 Jul 2013
Accepted
04 Sep 2013
First published
06 Sep 2013

CrystEngComm, 2013,15, 8572-8577
Article type
Paper

The competition between halogen bonds (Br⋯O) and C–H⋯O hydrogen bonds: the structure of the acetone–bromine complex revisited

R. H. Jones, K. S. Knight, W. G. Marshall, S. J. Coles, P. N. Horton and M. B. Pitak, CrystEngComm, 2013, 15, 8572
DOI: 10.1039/C3CE41472H

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