(E)-4-Hydroxy-6-methyl-3-[1-(2-phenylhydrazinylidene)ethyl]-2H-pyran-2-one

Samra Rahmouni,Amel Djedouani,Abderrahmen Bendaas,Solenne Fleutot,Rachid Touzani

doi:10.1107/s241431461600729x

Abstract

The title compound, C14H14N2O3, crystallized with three crystallographically independent molecules (A,BandC) in the asymmetric unit. The three molecules each have anEconformation about the C=N bond but differ in the orientation of the phenyl and pyran rings. The dihedral angles between the phenyl and pyran ring planes are 14.30 (1), 28.38 (1) and 25.58 (1)° in moleculesA,BandC, respectively. There is an intramolecular O—H...N hydrogen bond in each molecule with anS(6) ring motif. In the crystal, molecules are linked by N—H...O and C—H...O hydrogen bonds, forming layers parallel to (001), enclosingR22(8) andR33(21) ring motifs. The layers are linkedviaC—H...π interactions, forming bilayers, which are joined by a further C—H...π interaction, forming a three-dimensional structure.

Highlights

The title compound, C14H14N2O3, crystallized with three crystallographically independent molecules (A, B and C) in the asymmetric unit
The dihedral angles between the phenyl and pyran ring planes are 14.30 (1), 28.38 (1) and 25.58 (1) in molecules A, B and C, respectively
Molecules are linked by N—HÁ Á ÁO and C—HÁ Á ÁO hydrogen bonds, forming layers parallel to (001), enclosing R22(8) and R33(21) ring motifs

Summary

Structure description

Hydrazones have received much attention recently due to their biological activities (Ajani et al, 2010). The principle aim of investigating the structural chemistry of hydrazones is to study their coordination properties (Garcia-Herbosa et al 1994). We describe the synthesis and crystal structure of a new hydrazone ligand. The dihedral angles between the phenyl and pyran ring planes are 14.30 (1), 28.38 (1) and 25.58 (1), in molecules A, B and C, respectively. (Z)-ethyl 4-chloro-2-[2-(2-methoxyphenyl) hydrazono]-3oxobutanoate [1.300 (2) A ; Alpaslan et al, 2005c]. This elongation may be the result of the intramolecular O—HÁ Á ÁN hydrogen bonds that occur in each molecule C14H14N2O3 258.27 Monoclinic, C2/c 293 30.1064 (12), 17.5911 (7), 13.7937 (8) 92.613 (4) 7297.6 (6) 24 Mo K 0.10 0.1 Â 0.1 Â 0.1

No of parameters

Crystal data

Data collection

Special details