Solvatomorphism in 3-fluorobenzoylaminophenyl 3-fluorobenzoate: A subtle interplay of strong hydrogen bonds and weak intermolecular interactions involving disordered fluorine

3-Fluorobenzoylaminophenyl 3-fluorobenzoate crystallizes in dimorphic forms, generated by a delicate balance of strong and weak intermolecular forces, one form containing a trapped cyclohexane molecule in the crystalline lattice. Both forms crystallize as triclinic systems with centrosymmetric space group P (1) over bar. The supramolecular features in both forms is guided by control of strong N-H center dot center dot center dot O hydrogen bonds, weak but directional C-H center dot center dot center dot O and C-H center dot center dot center dot F interactions involving disordered fluorine, and isotropic C-H center dot center dot center dot pi and aromatic pi center dot center dot center dot pi stacking interactions that differentiate the packing in the two forms. The extent of disorder associated with organic fluorine is different in both forms.