Crystal structure and Hirshfeld surface analysis of 3-[2-(3,5-di-methyl-phen-yl)hydrazinyl-idene]benzo-furan-2(3H)-one.

Zeliha Atioğlu,Ajaya Bhattarai,Rizvan K Askerov,Sevinc H Mukhtarova,Namiq Q Shikhaliyev,Ulviyya F Askerova,Mehmet Akkurt

doi:10.1107/s2056989021011749

Abstract

In the title compound, C16H14N2O2, the 2,3-di-hydro-1-benzo-furan ring system is essentially planar and makes a dihedral angle of 3.69 (7)° with the di-methyl-phenyl ring. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond with an S(6) ring motif. In the crystal, mol-ecules are connected by C-H⋯π and π-π stacking inter-actions, forming a layer lying parallel to the (11) plane. One methyl group is disordered over two orientations, with occupancies of 0.67 (4) and 0.33 (4). Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (51.2%), O⋯H/H⋯O (17.9%), C⋯H/H⋯C (15.2%) and C⋯C (8.1%) contacts.

Highlights

The molecular conformation is stabilized by an intramolecular N— HÁ Á ÁO hydrogen bond with an S(6) ring motif
The molecular conformation of the title compound is stabilized by an intramolecular N—HÁ Á ÁO hydrogen bond (N2— H2Á Á ÁO2; Table 1) with an S(6) ring motif (Fig. 1)
The aromatic C9–C14 ring and the C N—NH– unit are almost coplanar with a dihedral angle of 4.8 (8) between them

Summary

Chemical context

Hydrazones have many applications in diverse areas, such as in optical data storage, as molecular switches and antimicrobial agents, in non-linear optics, molecular recognition, dye-sensitized solar cells, color-changing materials, catalysis, liquid crystals, etc., mainly because of the azo-to-hydrazo tautomerism/isomerism and the optical properties of –N N– unit (Maharramov et al, 2018; Ma et al, 2020, 2021; Viswanathan et al, 2019). The functional properties of hydrazones or their metal complexes can be regulated by attaching functional groups to the N—NH— unit (Gurbanov et al, 2020a,b; Kopylovich et al, 2011; Mahmudov et al, 2020; Shixaliyev et al, 2014). We have attached C O groups and furan and aryl rings to the N—NH— moiety, leading to a new hydrazone compound, (Z)-3-[2-(3,5dimethylphenyl)hydrazinylidene]benzofuran-2(3H)-one, which can form intermolecular interactions. Codes: (ii) Àx + 1, Ày + 1, Àz + 1; (iii) Àx + 2, Ày + 1, Àz + 2], where Cg1 and Cg2 are the centroids of the oxolane O1/C1– C3/C8 and benzene C3–C8 rings, respectively, of the 2,3-di-

Structural commentary

Supramolecular features

Hirshfeld surface analysis

Findings

Refinement details