N,N′-Diethyl-4-nitro-benzene-1,3-diamine, 2,6-bis-(ethyl-amino)-3- nitro-benzonitrile and bis-(4-ethyl-amino-3-nitro-phenyl) sulfone

Thomas J. Payne, Chad R. Thurman, Hao Yu, Qian Sun, Dillip K. Mohanty, Philip J. Squattrito, Mark Robin Giolando, Christopher R. Brue, Kristin Kirschbaum

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N,N′-Diethyl-4-nitro-benzene-1,3-diamine, C10H 15N3O3, (I), crystallizes with two independent mol-ecules in the asymmetric unit, both of which are nearly planar. The mol-ecules differ in the conformation of the ethyl-amine group trans to the nitro group. Both mol-ecules contain intra-molecular N - H⋯O hydrogen bonds between the adjacent amine and nitro groups and are linked into one-dimensional chains by inter-molecular N - H⋯O hydrogen bonds. The chains are organized in layers parallel to (101) with separations of ca 3.4 Å between adjacent sheets. The packing is quite different from what was observed in isomeric 1,3-bis-(ethyl-amino)-2-nitro-benzene. 2,6-Bis(ethyl-amino) -3-nitro-benzonitrile, C11H14N4O2, (II), differs from (I) only in the presence of the nitrile functionality between the two ethyl-amine groups. Compound (II) crystallizes with one unique mol-ecule in the asymmetric unit. In contrast with (I), one of the ethyl-amine groups, which is disordered over two sites with occupancies of 0.75 and 0.25, is positioned so that the methyl group is directed out of the plane of the ring by approximately 85°. This ethyl-amine group forms an intra-molecular N - H⋯O hydrogen bond with the adjacent nitro group. The packing in (II) is very different from that in (I). Mol-ecules of (II) are linked by both inter-molecular amine-nitro N - H⋯O and amine-nitrile N - H⋯N hydrogen bonds into a two-dimensional network in the (10 ) plane. Alternating mol-ecules are approximately orthogonal to one another, indicating that π-π inter-actions are not a significant factor in the packing. Bis(4-ethyl-amino-3-nitro-phenyl) sul-fone, C16H18N 4O6S, (III), contains the same ortho nitro/ethyl-amine pairing as in (I), with the position para to the nitro group occupied by the sulfone instead of a second ethyl-amine group. Each 4-ethyl-amino-3-nitro- benzene moiety is nearly planar and contains the typical intra-molecular N - H⋯O hydrogen bond. Due to the tetra-hedral geometry about the S atom, the mol-ecules of (III) adopt an overall V shape. There are no inter-molecular amine-nitro hydrogen bonds. Rather, each amine H atom has a long (H⋯O ca 2.8 Å) inter-action with one of the sulfone O atoms. Mol-ecules of (III) are thus linked by amine-sulfone N - H⋯O hydrogen bonds into zigzag double chains running along [001]. Taken together, these structures demonstrate that small changes in the functionalization of ethyl-amine-nitro-arenes cause significant differences in the inter-molecular inter-actions and packing.

Original languageEnglish
Pages (from-to)o369-o373
JournalActa Crystallographica Section C: Crystal Structure Communications
Issue number7
StatePublished - 2010


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