Co-crystal of carbazole-based thiourea derivative compound with acetic acid: Crystallography and Hirshfeld surface analysis

Abstract

Co-crystal of the N,N´-(((3,6-dichloro-9H-carbazole-1,8-diyl)bis(azanediyl))bis(carbonothioyl))bis(2,2dimethylpropanamide) as a carbazole-based thiourea derivative (CBT) with acetic acid (AcOH) was prepared and its molecular structure examined using the single crystal X-ray diffraction study and the Hirshfeld surface analysis. The co-crystal was designed to explore the supramolecular synthons and intermolecular interactions diversity between the components of co-crystal. The analysis of the crystal structure and packing revealed that the CBT:AcOH cocrystal are formed by a strong O-H⋯S and C-H•••O hydrogen bonding interactions between components of cocrystal. In addition, its' structure is further stabilized by strong C-H•••π stacking interactions and N-H•••O and N-H•••S homosynthons between CBT molecules. The Hirshfeld surfaces and associated two-dimensional fingerprint plots of the co-crystal were also analyzed to clarify the nature of the hydrogen bond interactions and close intermolecular interactions in the crystal structure. The Hirshfeld surfaces and the associated two-dimensional fingerprint plots analysis revealed that the majority of close contacts forming supramolecular structure were associated with relatively weak interactions such as H•••H, C•••H and N•••H. So, it can be said that these interactions play a major role in molecular crystal packing.