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

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)& sdot;& sdot;& sdot;N(thiazolyl) hydrogen bonds and face-to-face pi & sdot;& sdot;& sdot;pi 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)& sdot;& sdot;& sdot;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 & sdot;& sdot;& sdot;O(nitro), C-H & sdot;& sdot;& sdot;O(nitro), C-H & sdot;& sdot;& sdot;O(sulfonyl), C-H & sdot;& sdot;& sdot;pi, N = O & sdot;& sdot;& sdot;pi, S = O & sdot;& sdot;& sdot;pi, face-to-face pi & sdot;& sdot;& sdot;pi, and S & sdot;& sdot;& sdot;S interactions. A survey was carried out on the arrangements of (O2)S-NH-NH-C fragments in R/S(O2)NHNHCOR compounds.