Syntheses, Crystal Structure, Hirshfeld Surface Analyses of Cocrystals and Salt of a Flexible Imidazole Tethered Naphthalenediimide with Some Organic Acids

Abstract

One salt and three cocrystals of 2,7-bis(3-(1H-imidazol-1-yl)propyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone (L) have been synthesized and reported. 3-Nitro benzoic acid (3NBA) forms salt with L and 4-Nitro benzoic acid (4NBA), 4-hydroxy benzoic acid (4HBA) and 4-amino benzoic acid (4ABA) form cocrystals with L. L forms 1:1 salt with 3-NBA and 1:1 cocrystal with 4-NBA, 4-HBA and 4-ABA, respectively. All the complexes were formed in a warm solvent condition. The solid-state structures were determined by single crystal X-ray diffraction method. Salt 1 exhibits zig zag tetrameric water cluster in the solid-state structure. Various types of supramolecular interactions such as O–H⋯O, C–H⋯O, π⋯π, and C–H⋯π were observed in the X-ray structures and all these interactions guide the formation of 3D supramolecular architecture in the solid state of all the complexes. Besides, the 2D fingerprint (2D-FP) and Hirshfeld surface analysis (HSA) computations were served to prove the 2D network packed crystal lattice interactions.