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Co-crystal of the N , N ´-(((3,6-dichloro-9 H -carbazole-1,8-diyl) bis (azanediyl)) bis (carbonothioyl)) bis (2,2-dimethylpropanamide) 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. This 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 co-crystal are formed by a strong O–H ⋯ S and C-H ··· O hydrogen bonding interactions between components of co-crystal. 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.

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