Acta Cryst. (2002). B58, 701-709 [ doi:10.1107/S0108768102007978 ]
nitro interactions and aromatic ![[bold pi]](/logos/entities/pi_bdgif.gif)
stacking interactions in iodo-nitroanilinesAbstract: Molecules of 2-iodo-5-nitroaniline (I) are linked by N-HO hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodonitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitroaniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodonitro interactions into sheets of two types, each containing only a single type of molecule: stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N-HO hydrogen bonds and two distinct two-centre iodonitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.
Keywords: iodonitro interactions; stacking interactions; 2-iodo-5-nitroaniline; 4-iodo-2-nitroaniline; 2,4-diiodo-3-nitroaniline.
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| Structure factor file (CIF format) (168.1 kbytes) |
| Structure factor file (CIF format) (105.5 kbytes) |
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