Interplay of hydrogen bonding and π-stacking interactions in the solid-state architecture of pranoprofen: insights from X-ray crystallography and computational analyses

Abstract

We report the crystal structure of the anhydrous form of pranoprofen, a valuable non-steroidal anti-inflammatory drug, solved by direct space methodologies from synchrotron X-ray powder diffraction data. Through a detailed joint experimental and computational study we have explored the complex interplay of aromatic and hydrogen-bonding interactions present in the molecular arrangement of pranoprofen in the solid state. Cooperativity and reinforcement of π-stacking and hydrogen bonding interactions govern the singular crystal packing of pranoprofen, suggesting potential binding mechanisms with biological targets.