Comparison of halogen bonding and van der Waals and Pi-Pi interactions in 4,5-dibromo-2-hexyloxyphenol

FABIO D. CUKIERNIK; FLORENCIA CECCHI; RICARDO BAGGIO

ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS

International Union of Crystallography

Año: 2009 vol. 65 p. 233 - 236

0108-2701

The title compound, C12H16BrO2, is an interesting case of a simple organic molecule making use of .ve different types of intra- and intermolecular interactions (viz. conventional and nonconventional hydrogen bonds, and Pi–Pi, Br...Br and Br...O contacts), all of them relevant in the molecular and crystal structure geometry. The molecules are strictly planar, with an intramolecular O—H...O hydrogen bond, and associate into two-dimensional structures parallel to (201) through two different types of halogen bonding. The planar structures, in turn, stack parallel to each other interlinked by C—H...Pi and Pi–Pi contacts. Also discussed are the relevant structural features leading to the rather low melting point of the compound.12H16BrO2, is an interesting case of a simple organic molecule making use of .ve different types of intra- and intermolecular interactions (viz. conventional and nonconventional hydrogen bonds, and Pi–Pi, Br...Br and Br...O contacts), all of them relevant in the molecular and crystal structure geometry. The molecules are strictly planar, with an intramolecular O—H...O hydrogen bond, and associate into two-dimensional structures parallel to (201) through two different types of halogen bonding. The planar structures, in turn, stack parallel to each other interlinked by C—H...Pi and Pi–Pi contacts. Also discussed are the relevant structural features leading to the rather low melting point of the compound.