N′-(1,3-Benzothiazol-2-yl)benzenesulfonohydrazide: crystal structure, Hirshfeld surface analysis and computational chemistry

The asymmetric unit of the title compound, CHNOS, comprises two independent mol-ecules ( and ); the crystal structure was determined by employing synchrotron radiation. The mol-ecules exhibit essentially the same features with an almost planar benzo-thia-zole ring (r.m.s. deviation = 0.026 and 0.009 Å for and , respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the mol-ecules is noted in a twist about the N-S bonds [the C-S-N-N torsion angles = -56.2 (5) and -68.8 (5)°, respectively], which leads to a minor difference in orientation of the phenyl rings. In the mol-ecular packing, and are linked into a supra-molecular dimer pairwise hydrazinyl-N-H⋯N(thiazol-yl) hydrogen bonds. Hydrazinyl-N-H⋯O(sulfon-yl) hydrogen bonds between mol-ecules assemble the dimers into chains along the -axis direction, while links between centrosymmetrically related mol-ecules, leading to eight-membered {⋯HNSO} synthons, link the mol-ecules along [001]. The result is an undulating supra-molecular layer. Layers stack along the -axis direction with benzo-thia-zole-C-H⋯O(sulfon-yl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above inter-molecular inter-actions, but also serve to further differentiate the weaker inter-molecular inter-actions formed by the independent mol-ecules, such as π-π inter-actions. This is also highlighted in distinctive energy frameworks calculated for the individual mol-ecules.