Acta Crystallographica Section B

Structural Science

Volume 62, Part 4 (August 2006)

research papers

Acta Cryst. (2006). B62, 666-675 [ doi:10.1107/S010876810601439X ]

Isomers and polymorphs of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadienes

C. Glidewell, J. N. Low, J. M. S. Skakle and J. L. Wardell

Abstract: The structures of five of the possible six isomers of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadiene are reported, including two polymorphs of one of the isomers. (E,E)-1,4-Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene, C₁₄H₁₀N₄O₄ (I), crystallizes in two polymorphic forms (Ia) and (Ib) in which the molecules lie across centres of inversion in space groups P2₁/n and P2₁/c, respectively: the molecules in (Ia) and (Ib) are linked into chains by aromatic [pi] [pi] stacking interactions and C-H [pi] (arene) hydrogen bonds, respectively. Molecules of (E,E)-1-(2-nitrophenyl)-4-(3-nitrophenyl)-2,3-diaza-1,3-butadiene (II) are linked into sheets by two independent C-HO hydrogen bonds. The molecules of (E,E)-1,4-bis(3-nitrophenyl)-2,3-diaza-1,3-butadiene (III) lie across inversion centres in the space group P2₁/n, and a combination of a C-HO hydrogen bond and a [pi] [pi] stacking interaction links the molecules into sheets. A total of four independent C-HO hydrogen bonds link the molecules of (E,E)-1-(3-nitrophenyl)-4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene (IV) into sheets. In (E,E)-1,4-bis(4-nitrophenyl)-2,3-diaza-1,3-butadiene (V) the molecules, which lie across centres of inversion in the space group P2₁/n, are linked by just two independent C-HO hydrogen bonds into a three-dimensional framework.

Keywords: supramolecular structures; direction-specific intermolecular interactions; polymorphism; hydrogen bonding.


	Structure factor file (CIF format) (74.8 kbytes) [ doi:10.1107/S010876810601439X/bm5032Iasup2.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

	Structure factor file (CIF format) (74.4 kbytes) [ doi:10.1107/S010876810601439X/bm5032Ibsup3.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

	Structure factor file (CIF format) (146.8 kbytes) [ doi:10.1107/S010876810601439X/bm5032IIsup4.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

	Structure factor file (CIF format) (74.4 kbytes) [ doi:10.1107/S010876810601439X/bm5032IIIsup5.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

	Structure factor file (CIF format) (194.3 kbytes) [ doi:10.1107/S010876810601439X/bm5032IVsup6.fcf ] Contains datablock {vcif WARNING: Line 0: length exceeds internal buffer size (1024) - rest discarded}

	Structure factor file (CIF format) (73.2 kbytes) [ doi:10.1107/S010876810601439X/bm5032Vsup7.fcf ] Contains datablock V

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