Charge-Assisted Hydrogen Bonds and Halogen-Halogen Interactions in Organic Salts: Benzylammonium Benzoates and Pentafluorobenzoates

The enhanced influence of charge-assisted hydrogen bonds upon the resulting crystal structure in the presence of competing noncovalent interactions has been examined using single-crystal X-ray diffraction. The crystal structures of six organic salts are presented: 4-chlorobenzylammonium 2,4-dichlorobenzoate, 3-chlorobenzylammonium 2,4-dichlorobenzoate, 4-methylbenzylammonium pentafluorobenzoate, 4-chlorobenzylammonium pentafluorobenzoate, 3-methylbenzylammonium benzoate, and 4-chlorobenzylammonium benzoate monohydrate. All structures are dominated by charge-assisted hydrogen bonds that generate either one-dimensional ribbons or two-dimensional sheets. The structural influence of weaker intermolecular interactions is limited as there are very few short, halogen-halogen, -, or distances in this series of compounds.