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Acta Crystallographica Section E: Crystallographic Communications, vol.81, pp.314-323, 2025 (ESCI)
Molecules of the title compounds, methyl (Z)-2-(4-bromophenyl)-2-[2-(4-methylphenyl)hydrazin-1-ylidene]acetate, C16H15BrN2O2, (1), methyl (Z)-2-(4-bromophenyl)-2-[2-(3,5-dimethylphenyl)hydrazin-1-ylidene]acetate, C17H17BrN2O2, (2), methyl (Z)-2-[2-(4-methoxyphenyl)hydrazin-1-ylidene]-2-(3-nitrophenyl)acetate, C16H15N3O5, (3), and methyl (Z)-2-[2-(4-bromophenyl)hydrazin-1-ylidene]-2-(4-chlorophenyl)acetate, C15H12BrClN2O2, (5), adopt a Z configuration with respect to the central C=N bond, while methyl (E)-2-(4-chlorophenyl)-2-(2-phenylhydrazin-1-ylidene)acetate, C15H13ClN2O2, (4), adopts an E configuration. The atoms of the phenyl ring of the bromophenyl group of (1) are disordered over two sets of sites with equal occupancies. In the crystal structure of (1), molecules connected by C - H⋯N hydrogen bonds are further linked by C - H⋯π interactions, forming ribbons parallel to [010]. In (2), pairs of molecules are linked by C - H⋯π interactions parallel to [100]. In (3), C - H⋯O hydrogen bonds form ribbons parallel to [010], while in (4), the molecules are bonded together by C - H⋯N, C - H⋯Cl, C - H⋯O and C - H⋯π interactions parallel to [010]. In (5), C - H⋯Br, C - H⋯O and C - H⋯Cl interactions lead to the formation of layers parallel to (002). C - H⋯π interactions also occur between these planes. Hirshfeld surface analyses were performed to investigate and quantify the intermolecular interactions between the molecules of all compounds.