Crystal structure and Hirshfeld surface analysis of 1-(2,4-dichlorobenzyl)-5-methyl-N-(thiophene-2-sulfonyl)-1H-pyrazole-3-carboxamide


Aydın A., Akkurt M., Gür Maz Z. T. , Banoğlu E.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.74, pp.747-757, 2018 (Peer-Reviewed Journal) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 74
  • Publication Date: 2018
  • Doi Number: 10.1107/s2056989018006242
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index, Scopus
  • Page Numbers: pp.747-757
  • Keywords: crystal structure, dimer, 1H-pyrazole ring, thiophene ring, disorder, hydrogen-bonding patterns, PYRAZOLE CARBOXAMIDE, DERIVATIVES, ACID, INHIBITORS

Abstract

In the title compound, C16H13Cl2N3O3S2, the thiophene ring is disordered in a 0.762(3):0.238(3) ratio by an approximate 180 degrees rotation of the ring around the S-C bond linking the ring to the sulfonyl unit. The dichlorobenzene group is also disordered over two sets of sites with the same occupancy ratio. The molecular conformation is stabilized by intramolecular C-H center dot center dot center dot Cl and C-H center dot center dot center dot N hydrogen bonds, forming rings with graph-set notation S(5). In the crystal, pairs of molecules are linked by N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds, forming inversion dimers with graph-set notation R-2(2)(8) and R-1(2)(11), which are connected by C-H center dot center dot center dot O hydrogen-bonding interactions into ribbons parallel to (100). The ribbons are further connected into a three-dimensional network by C-H center dot center dot center dot pi interactions and pi-pi stacking interactions between benzene and thiophene rings, with centroid-to-centroid distances of 3.865(2), 3.867 (7) and 3.853 (2) angstrom. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions.