CRYSTAL STRUCTURE OF 2-BROMO-4-HYDROXYPYRIDINE: HYDROGEN AND HALOGEN BONDING

Jeffrey C. Monroe, Mark M. Turnbull

Abstract


The crystal structure of 2-bromo-4-hydroxypyridine(1)at 120 K is reported.  The compound crystallizes in the monoclinic space group C2/c with a = 15.6770(6) Å, b = 3.86471(13) Å, c = 18.0645(7) Å and β = 90.916(3)°.  The compound exhibits both the 4-hydroxypyridine and 4-pyridone tautomers as exhibited by the disordered proton which occupies the O-H and N-H positions equally.  Hydrogen bonding links the molecules into chains parallel to the ac-face diagonal.  Halogen bonds [Br … O = 3.0809(15) Å] roughly parallel to the a-axis link the chains into layers roughly parallel to the bc-face diagonal.  π-stacking interactions complete the stabilization of the structure.

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DOI: http://dx.doi.org/10.17628/ecb.2019.8.203-206

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