Acta Crystallographica Section B

Structural Science

Volume 63, Part 1 (February 2007)

research papers

Acta Cryst. (2007). B63, 101-110 [ doi:10.1107/S0108768106041358 ]

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

S. M. S. V. Wardell, M. V. N. de Souza, J. L. Wardell, J. N. Low and C. Glidewell

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 [pi] [pi] 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 [pi] [pi] 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.

Keywords: geometrical isomers; hydrogen bonding; phenylhydrazine; polymorphism; supramolecular structures.


	Structure factor file (CIF format) (126.4 kbytes) [ doi:10.1107/S0108768106041358/ws5049Iasup2.fcf ] Contains datablock Ia

	Structure factor file (CIF format) (129.1 kbytes) [ doi:10.1107/S0108768106041358/ws5049Ibsup3.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

	Structure factor file (CIF format) (140.2 kbytes) [ doi:10.1107/S0108768106041358/ws5049Icsup4.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

	Structure factor file (CIF format) (139.8 kbytes) [ doi:10.1107/S0108768106041358/ws5049IIsup5.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

	Structure factor file (CIF format) (125.3 kbytes) [ doi:10.1107/S0108768106041358/ws5049IIIsup6.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

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