Affiliations 

  • 1 Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland
  • 2 Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, RJ, Brazil
  • 3 Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India
  • 4 Research Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
Acta Crystallogr E Crystallogr Commun, 2019 Apr 01;75(Pt 4):516-523.
PMID: 31161067 DOI: 10.1107/S2056989019003980

Abstract

The asymmetric unit of the title compound, C13H11N3O2S2, comprises two independent mol-ecules (A and B); 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 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 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, A and B are linked into a supra-molecular dimer via pairwise hydrazinyl-N-H⋯N(thiazol-yl) hydrogen bonds. Hydrazinyl-N-H⋯O(sulfon-yl) hydrogen bonds between A mol-ecules assemble the dimers into chains along the a-axis direction, while links between centrosymmetrically related B mol-ecules, leading to eight-membered {⋯HNSO}2 synthons, link the mol-ecules along [001]. The result is an undulating supra-molecular layer. Layers stack along the b-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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.