Structural Characterization of Multicomponent Crystals Formed from Diclofenac and Acridines

Abstract

Multicomponent crystals containing diclofenac and acridine (1) and diclofenac and 6,9-diamino-2-ethoxyacridine (2) were synthesized and structurally characterized. The single-crystal XRD measurements showed that compound 1 crystallizes in the triclinic P-1 space group as a salt cocrystal with one acridinium cation, one diclofenac anion, and one diclofenac molecule in the asymmetric unit, whereas compound 2 crystallizes in the triclinic P-1 space group as an ethanol solvate monohydrate salt with one 6,9-diamino-2-ethoxyacridinium cation, one diclofenac anion, one ethanol molecule, and one water molecule in the asymmetric unit. In the crystals of the title compounds, diclofenac and acridines ions and solvent molecules interact via N–H· · · O, O–H· · · O, and C–H· · · O hydrogen bonds, as well as C–H· · · π and π–π interactions, and form heterotetramer bis[· · · cation· · · anion· · · ] (1) or heterohexamer bis[· · · cation· · · ethanol· · · anion· · · ] (2). Moreover, in the crystal of compound 1, acridine cations and diclofenac anions interact via N–H· · · O hydrogen bond, C–H· · · π and π–π interactions to produce blocks, while diclofenac molecules interact via C–Cl· · · π interactions to form columns. In the crystal of compound 2, the ethacridine cations interact via C–H· · · π and π–π interactions building blocks, while diclofenac anions interact via π–π interactions to form columns.