Crystal structure of 3-bromo-2-hy-droxy-benzo-nitrile.
The crystal structure of the title compound, C7H4BrNO, has been determined, revealing a partial mol-ecular packing disorder such that a 180° rotation of the mol-ecule 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 intra-molecular 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 mol-ecules also inter-act, forming offset face-to-face π-stacking inter-actions with plane-to-centroid distance of 3.487 (1) Å.
Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.
Sean R
SR
Dickinson
X-Ray Diffraction Facility, MIT Department of Chemistry, 77 Massachusetts Avenue, Building 2, Room 325, Cambridge, MA, 02139-4307, USA.
Peter
P
Müller
Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.
Joseph M
JM
Tanski
crystal structure; disorder; hydrogen bonding; π-stacking