Three isomeric 1-(2-chloronicotinoyl)-2-(nitrophenyl)hydrazines, including three polymorphs of 1-(2-chloronicotinoyl)-2-(2-nitrophenyl)hydrazine:hydrogen-bonded supramolecular structures intwo and three dimensions

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Abstract

1-(2-Chloronicotinoyl)-2-(2-nitrophenyl)hydrazine, C₁₂H₉Cl­N₄O₃, crystallizes in three polymorphic forms, two monoclinic forms in space groups Cc (Ia) and P2₁ (Ib), and an orthorhombic form in space group Pbcn (Ic). In the Cc polymorph (Ia) the molecules are linked into sheets by combinations of one N-HO and two C-HO hydrogen bonds, while in the P2₁ polymorph (Ib) the molecules are linked into sheets by combinations of three hydrogen bonds, one each of N-HO, C-HN and C-HO types. In the orthorhombic polymorph (Ic) the molecules are linked into a complex three-dimensional framework structure by a combination of one N-HO, one N-HN and three C-HO hydrogen bonds, and an aromatic stacking interaction. In the isomeric compound 1-(2-chloronicotinoyl)-2-(3-nitrophenyl)hydrazine (II) the molecules are again linked into a three-dimensional framework, this time by a combination of three hydrogen bonds, one each of N-HO, N-HN and C-HO types, weakly augmented by a stacking interaction. The molecules of 1-(2-chloronicotinoyl)-2-(4-nitrophenyl)hydrazine (III) are linked into sheets by a combination of three hydrogen bonds, one each of N-HO, N-HN and C-HO types.

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Keywords: None Document Type: Research Article DOI: http://dx.doi.org/10.1107/S0108768106041358 Publication date: 1 de Janeiro de 2007