Acta Crystallographica Section C

Crystal Structure Communications

Volume 65, Part 2 (February 2009)

organic compounds

 

4,6-Dinitro-N,N'-di-n-octylbenzene-1,3-diamine, 4,6-dinitro-N,N'-di-n-undecylbenzene-1,3-diamine and N,N'-bis(2,4-dinitrophenyl)octane-1,8-diamine

G. Teng, C. P. Walczak, P. J. Squattrito, D. K. Mohanty, W. Scharer, M. R. Giolando and K. Kirschbaum

Abstract: 4,6-Dinitro-N,N'-di-n-octylbenzene-1,3-diamine, C₂₂H₃₈N₄O₄, (I), 4,6-dinitro-N,N'-di-n-undecylbenzene-1,3-diamine, C₂₈H₅₀N₄O₄, (II), and N,N'-bis(2,4-dinitrophenyl)octane-1,8-diamine, C₂₀H₂₄N₆O₈, (III), are the first synthetic meta-dinitroarenes functionalized with long-chain aliphatic amine groups to be structurally characterized. The intra- and intermolecular interactions in these model compounds provide information that can be used to help understand the physical properties of corresponding polymers with similar functionalities. Compounds (I) and (II) possess near-mirror symmetry, with the octyl and undecyl chains adopting fully extended anti conformations in the same direction with respect to the ring. Compound (III) rests on a center of inversion that occupies the mid-point of the central C-C bond of the octyl chain. The middle six C atoms of the chain form an anti arrangement, while the remaining two C atoms take hard turns almost perpendicular to the rest of the chain. All three molecules display intramolecular N-HO hydrogen bonds between the amine and nitro groups, with the same NH group forming a bifurcated intermolecular hydrogen bond to the nitro O atom of an adjacent molecule. In each case, these interactions link the molecules into one-dimensional molecular chains. In (I) and (II), these chains pack so that the pendant alkyl groups are interleaved parallel to one another, maximizing nonbonded C-H contacts. In (III), the alkyl groups are more isolated within the molecular chains and the primary nonbonded contacts between the chains appear to involve the nitro groups not involved in the hydrogen bonding.

Formula: C₂₂H₃₈N₄O₄, C₂₈H₅₀N₄O₄ and C₂₀H₂₄N₆O₈

	Structure factor file (CIF format) (276.4 kbytes) [ doi:10.1107/S0108270109001619/sk3288Isup2.hkl ] Contains datablock I
	Structure factor file (CIF format) (280.3 kbytes) [ doi:10.1107/S0108270109001619/sk3288IIsup3.hkl ] Contains datablock II
	Structure factor file (CIF format) (103.1 kbytes) [ doi:10.1107/S0108270109001619/sk3288IIIsup4.hkl ] Contains datablock III

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