Crystal structure of 3-bromo-2-hydroxybenzonitrile

Abstract

The crystal structure of the title compound, C7H4BrNO, has been determined, revealing a partial molecular packing disorder such that a 180° rotation of the molecule about the phenol C—O bond results in disorder of the bromine and nitrile groups. The disorder has been parameterized as a disorder of only the bromine and nitrile substituents on a unique phenol ring. An intramolecular O—H...Br contact occurs. In the crystal, O—H...Br/O—H...Nnitrile hydrogen bonding is present between the disordered bromine and nitrile substituents and the phenol group, forming a spiral chain about a twofold screw axis extending parallel to the b-axis direction. Within this spiral chain, the molecules also interact, forming offset face-to-face π-stacking interactions with plane-to-centroid distance of 3.487 (1) Å.

Keywords

• crystal structure
• disorder
• hydrogen bonding
• π-stacking