  Polyhalogenated compounds are common in industrial, agricultural, and
environmental applications. These compounds contain more halogen bonds than
monohalogenated compounds. The presence of coupled {\sigma}-holes in the
covalent halogen atoms, which demonstrates strong interplay in halogen bonds,
should be carefully evaluated in force field optimization. In this study, a
polarizable ellipsoidal force field model was successfully applied to many
possible halogenated benzenes. The symmetry of the fitted parameters was
reproduced without any additional restrictions. The optimized parameters for
the anisotropic electrostatic potential showed good accuracy, stability, and
transferability with reasonable physical meanings. The parameter fitting
protocol was efficiently performed on a laptop, showing the potential of being
completely parallelized for thousands of halogenated homologues.
