Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl] diazene


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Shikhaliyev N. Q. , Celikesir S. T. , AKKURT M. , Bagirova K. N. , Suleymanova G. T. , Toze F. A. A.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.75, pp.465-473, 2019 (Journal Indexed in ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 75
  • Publication Date: 2019
  • Doi Number: 10.1107/s2056989019003657
  • Title of Journal : ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Page Numbers: pp.465-473

Abstract

In the title compound, C14H8Cl3FN2, the planes of the 4-fluorophenyl ring and the 4-chlorophenyl ring make a dihedral angle of 56.13 (13)degrees. In the crystal, molecules are stacked in a column along the a axis via a weak C-H center dot center dot center dot Cl hydrogen bond and face-to-face pi-pi stacking interactions [centroid-centroid distances = 3.8615 (18) and 3.8619 (18) angstrom]. The crystal packing is further stabilized by short Cl center dot center dot center dot Cl contacts. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from Cl center dot center dot center dot H/H center dot center dot center dot Cl (31.2%), H center dot center dot center dot H (14.8%), C center dot center dot center dot H/H center dot center dot center dot C (14.0%), F center dot center dot center dot H/H center dot center dot center dot F (12.8%), C center dot center dot center dot C (9.0%) and Cl center dot center dot center dot Cl (6.7%) interactions.