Crystal structure and Hirshfeld surface analysis of (2 Z)- N, N-dimethyl-2-(penta-fluoro-phen-yl)-2-(2-phenyl-hydrazin-1-yl-idene)acetamide

Acta Crystallogr E Crystallogr Commun. 2021 Jul 23;77(Pt 8):829-833. doi: 10.1107/S2056989021007349. eCollection 2021 Aug 1.

Abstract

In the title compound, C16H12F5N3O, the dihedral angle between the aromatic rings is 31.84 (8)°. In the crystal, the mol-ecules are linked into dimers possessing crystallographic twofold symmetry by pairwise N-H⋯O hydrogen bonds and weak C-H⋯O hydrogen bonds and aromatic π-π stacking inter-actions link the dimers into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from F⋯H/H⋯F (41.1%), H⋯H (21.8%), C⋯H/H⋯C (9.7%) C⋯C (7.1%) and O⋯H/H⋯O (7.1%) contacts. The contribution of some disordered solvent to the scattering was removed using the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9-18] in PLATON. The solvent contribution was not included in the reported mol-ecular weight and density.

Keywords: Hirshfeld surface analysis; SQUEEZE; crystal structure; fluorine; hydrogen bonds; π–π stacking inter­actions.

Grants and funding

This work was funded by Science Development Foundation under the President of the Republic of Azerbaijan grant EIF-BGM-4- RFTF-1/2017-21/13/4.