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

Thomas C. Baddeley, Marcus V. N. de Souza, James L. Wardell (Corresponding Author), Mukesh M. Jotani, Edward R. T. Tiekink (Corresponding Author)

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The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent mol­ecules (Aand B); the crystal structure was determined by employing synchrotron radiation. The mol­ecules exhibit essentially the same features with an almost planar benzo­thia­zole ring (r.m.s. deviation = 0.026 and 0.009 Å for A and B, respectively), which forms an inclined dihedral angle with the phenyl ring [28.3 (3) and 29.1 (3)°, respectively]. A difference between the mol­ecules 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 mol­ecular packing, A and B are linked into a supra­molecular dimer via pairwise hydrazinyl-N—H⋯N(thiazol­yl) hydrogen bonds. Hydrazinyl-N—H⋯O(sulfon­yl) hydrogen bonds between A mol­ecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B mol­ecules, leading to eight-membered {⋯HNSO}2 synthons, link the mol­ecules along [001]. The result is an undulating supra­molecular layer. Layers stack along the b-axis direction with benzo­thia­zole-C—H⋯O(sulfon­yl) points of contact being evident. The analyses of the calculated Hirshfeld surfaces confirm the relevance of the above inter­molecular inter­actions, but also serve to further differentiate the weaker inter­molecular inter­actions formed by the independent mol­ecules, such as π–π inter­actions. This is also highlighted in distinctive energy frameworks calculated for the individual mol­ecules.


  • Hirshfeld surface analysis
  • benzothiazole
  • computational chemistry.
  • crystal structure
  • hydrogen bonding
  • sulfonylhydrazinyl


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