Structural systematics of 4,4'-disubstituted benzenesulfonamidobenzenes. 1. Overview and dimer-based isostructures

Gelbrich, T., Hursthouse, M.B. and Threlfall, T.L. (2007) Structural systematics of 4,4'-disubstituted benzenesulfonamidobenzenes. 1. Overview and dimer-based isostructures. Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 63, 621-632. (doi:10.1107/S010876810701395X).

Abstract

One hundred 4,4'-disubstituted benzenesulfonamidobenzenes, X-C6H5-SO2-NH-C6H5-Y, where X, Y = NO2, CN, CF3, I, Br, Cl, F, H, Me, OMe, have been synthesized and their crystal structures determined. The resulting set of 133 structures, which includes polymorphic forms, is used to make a comparative study of the molecular packing and the nature of the intermolecular interactions, including the formation of hydrogen-bonding motifs and the influence of the two substituents X and Y on these features. Nine distinct supramolecular connectivity motifs of hydrogen bonding are encountered. There are 74% of all the structures investigated which exhibit one of two motifs based on N-HO=S interactions, a dimer or a chain. There are three other, infrequent motifs, also employing N-HO=S links, which exhibit more complexity. Four different chain motifs result from either N-HO=N, N-HCN or N-HOMe interactions, arising from the presence of a nitro (position Y), nitrile (X or Y) or methoxy (Y) substituent. The program XPac [Gelbrich & Hursthouse (2005). CrystEngComm, 7, 324-336] was used to systematically analyse the packing relationships between crystal structures. Similar discrete (zero-dimensional) and extended (one-dimensional and two-dimensional) structure components, as well as cases of isostructurality were identified. A hierarchy for the classification of the 56 distinct structure types of this set is presented. The most common type, a series of 22 isostructures containing the simple centrosymmetric N-HO=S-bonded dimer, is discussed in detail.

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