The Role of Weak C–H···X (X = O, π) Interactions in Three 1-Hydroxy-2-naphthoic Acid Cocrystals with N-Containing Heteroaromatics: Structural Characterization and Synthon Cooperation

Herein, three novel cocrystals of 1-hydroxy-2-naphthoic acid: tetramethylpyrazine, acid:1,10-phenanthroline, and acid:1,4-bis(imidazol-1-ylmethyl)benzene (L2) were obtained by crystallization in methanol–water mixed solvent via a slow evaporation method. The cocrystalline products 1−3 carried out range techniques, including single-crystal X-ray diffraction, Fourier transform–infrared spectroscopy, elemental analysis, thermogravimetric testing. We analyzed the crystal structures found that weak interactions C–H···X (X = O or π) great importance process self-assembly as well strong conventional hydrogen bonds (N–H···O, O–H···N, O–H···O), leading to stable diverse multidimensional supramolecular architecture. It is worth noting series ring motifs with different sizes explored above complexes, such R22(5), R22(7), R22(8), R23(13), R24(16), R44(16), R44(22), so on. classical robust synthon intermolecular bond between acid pyridine (acid···pyridine) heterosynthon commonly organic solids containing carboxylic acids other N-containing heteroaromatics, was further demonstrated be involved construction hydrogen-bond networks cocrystal 1. technique used this study proved mass losses these closely related strength package fraction.