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.
Highlights
The molecules are linked into dimers possessing crystallographic twofold symmetry by pairwise N—HÁ Á ÁO hydrogen bonds and weak C—HÁ Á ÁO hydrogen bonds and aromatic – stacking interactions link the dimers into a three-dimensional network
A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from FÁ Á ÁH/HÁ Á ÁF (41.1%), HÁ Á ÁH (21.8%), CÁ Á ÁH/HÁ Á ÁC (9.7%) CÁ Á ÁC (7.1%) and OÁ Á ÁH/HÁ Á ÁO (7.1%) contacts
The three-dimensional Hirshfeld surface mapped over dnorm in the range À0.52 to 2.23 a.u. is shown in Fig. 3: the H9CÁ Á ÁF1, H16Á Á ÁF2, F3Á Á ÁH10C, H3NÁ Á ÁO1, N3—H3NÁ Á ÁO1 and C14—H14Á Á ÁO1 interactions, which play a key role in the molecular packing, can be correlated with the bright-red patches near F1, F2, F3 and O1 and hydrogen atoms H3N and H14, which highlight their functions as donors and/or acceptors
Summary
Arylhydrazones containing a (Ph,R)C N—NHR grouping possess controllable E/Z isomerization around the C N double bond, which makes them good candidates for the construction of functional materials (Ma et al, 2021). Control of the supramolecular chemistry of hydrazone ligands and the corresponding complexes may afford multi-dimensional synthons or metallo-organic tectons (Kopylovich et al, 2011; Gurbanov et al, 2020a). The functionalization of arylhydrazone ligands with groups such as –SO3H, –COOH, –F, –Cl, etc., can improve the catalytic or biological activity of the corresponding coordination compounds (e.g., Shikhaliyev et al, 2019; Gurbanov et al, 2020b). Symmetry codes: (i) Àx þ 1; y; Àz þ 32; (ii) x À 12; y À 12; z; (iii) Àx þ 12; Ày þ 32; Àz þ 1.
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