A thorough statistical analysis of the structures deposited in the Cambridge Structure Database reveals that both the lone-pair-π and anion-π interactions occur in a predictive and directional fashion, as evidenced by the careful examination of potential bonding contacts between some common solvent molecules or non-coordinating anions and the electron-rich phenyl or electron-deficient pentafluorophenyl rings. The general directional character of both the lone-pair-π and anion-π bonds is clearly observed in the solid state.
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Mooibroek et al. (2012) studied this question.
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