J. O. Bauer, Sarah Koschabek, Alexander Falk
Sep 2, 2021
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ChemistrySelect
Abstract
Hydrogen and halogen bonds are important anisotropic attractive interactions in the molecular crystalline state. 2,6-dibromophenol ( 1 ) was analyzed by single-crystal X-ray diffraction for the first time. The intermolecular interaction pattern was studied by Hirshfeld surface analysis along with 2D fingerprint diagrams. The characteristic interactions that domi-nate the crystal packing are electrostatic type-II Br ⋅⋅⋅ Br interactions, O (cid:0) H ⋅⋅⋅ O hydrogen bonds, and an offset parallel π stacking arrangement. Compound 1 was compared with 2,6-difluoro- ( 2 ) and 2-bromo-6-chlorophenol ( 3 ) in terms of their interplay between hydrogen and halogen bonding. Whereas the O (cid:0) H ⋅⋅⋅ O hydrogen bond is more pronounced in the lighter homologues, the halogen ⋅⋅⋅ halogen interaction becomes a particularly important directional, attractive interaction in the crystal structure of 2,6-dibromophenol. Spectroscopic data of compound 1 , details on X-ray crystallog-raphy including the crystal packing of compound 1 , molecular electrostatic potentials (ESPs) of compounds 1 – 3 , and details on quantum chemical calculations can be found in the Supporting Information.