Crystal packing of structurally similarand strong dimeric subunits of isomeric N/ -(1,3- benzothiazol-2-yl)nitrobenzenesulfonylhydrazides, influenced by the position of the nitro group

Abstract

Detailed structural analyses, utilizing single crystal X-ray diffraction, Hirshfeld surface analyses, PIXEL and electrostatic potentials calculations, have been carried out on three isomeric N/-(1,3-benzothiazol-2-yl)nitrobenzenesulfonylhydrazides, Bt-NHNHSO2C6H4NO2-o, m and p. These compounds each crystallize from ethanol solution with two independent, but similar, amino tautomers, in the asymmetric units. For all three compounds, similar and dominant dimeric unsymmetric sub-structures are present in the solid state, linked prominently by pairs of N—H(hydrazinyl)···N(thiazolyl) hydrogen bonds and face-to-face π···π interactions: these sub-structures are the motifs I for each compound. A significant consequence of the different positions of the nitro group in the phenyl ring is the presence of the intramolecular N—H(hydrazonyl)···O(nitro) hydrogen bond present in the ortho derivative, but absent in the meta and para isomers. Apart from this, the different sites of the nitro groups have only a small influence on the internal structure of these motifs I, however they do play a major role in their packing and connections with other motifs. Among the interactions connecting the motifs are N—H···O(nitro), C—H···O(nitro), C—H···O(sulfonyl), C—H···π,N = O···π, S = O···π, face-to-face π···π, and S···S interactions. A survey was carried out on the arrangements of (O2)S-NHNHC fragments in R/S(O2)NHNHCOR compounds.