Crystal structures and Hirshfeld surface analyses of methyl (2Z)-(4-bromo­phen­yl)[2-(4-methyl­phen­yl)hydrazinyl­idene]acetate, methyl (2Z)-(4-bromophen­yl)[2-(3,5-di­methyl­phen­yl)hydrazinyl­idene]acetate, methyl (2Z)-[2-(4-meth­oxy­phen­yl)hydrazinyl­idene](3-nitro­phen­yl)acetate, methyl (2E)-(4-chlorophen­yl)(2-phenyl­hydrazinyl­idene)acetate and methyl (2Z)-[2-(4-bromo­phen­yl)hydrazinylidene](4-chloro­phen­yl)acetate

Abstract

Mol­ecules (1), (2), (3) and (5) adopt a Z configuration with respect to the central C=N bond, while (4) adopts an E configuration.

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.