Source of materialToanethanol solution (5 ml) of 2 ¢ -hydroxyacetophenone (274.50 mg, 2.01 mmol) wasadded ane thanol solution (3 ml) of 1,4-bis-(aminooxy)butane (124.30 mg, 1.03 mmol). After the solution hadbeen stirred at55°Cfor 2h,the mixture wasfiltered. The residue wasw ashed successively with ethanol and ethanol/hexane (1:4),r espectively. The isolated compound wasd ried under reduced pressure and purified by recrystallization from ethanol to yield 119.10 mg of colorless crystallinesolid (yield 34 %, m.p. 132-133°C). The single crystals were obtained atRT by slow evaporationf rom amixture of tetrahydrofuran/methanol( 1:1, v / v ) and 2,2¢ -[(1,4-butylene)dioxybis(nitriloethylidyne)]-diphenol.
DiscussionParticularattention hasr ecently been paid to the synthesis and study of salen and its derivatives. This is due to avarietyofreasons, not the least of which is theircrucialrole in inorganic and organometallic chemistry, e.g., they caneasily form metallosalen complexes with metalions asversatile chelating ligands. Some of them or their metalcomplexes are used in various organic reaction processes asc atalysts [1], models of reaction centers of metalloenzymes [2], have fascinating magnetic properties [3] and are nonlinearopticalmaterials [4]. They canalso be used asbiologicalm odels in understanding the structure of biomolecules and biologicalprocesses [5,6]. Most of their important features of these compounds are their preparative accessibility, diversityand structuralv ariability, which make them more attractive. Although the important properties of salen and its derivatives have been well-documented, it still seems there could be new and specific applications for such aunique group of compounds. The salen ligandsinmost of their metalcomplexes are stable insolution or solid state, however, the C = Nbonds often suffer exchange reaction asw ell ash ydrolysis. Because the oxime-type ligandsare more stable to resist the metathesis of C = Nbonds
The molecule of the title compound, C19H22N2O6, assumes a W-shaped configuration with the dihedral angle between the two halves of the molecule being 82.48 (5)°. There is one half-molecule in the asymmetric unit with a crystallographic twofold rotation axis passing through the central C atom of the five methylene groups in the [—CH=N—O—(CH2)5—O—N=CH—] bridge. The dihedral angle formed by the two benzene rings in each molecule of the title compound is 84.18 (4)°. There are strong intramolecular O—H⋯N and O—H⋯O hydrogen bonds and weak intermolecular π–π stacking interactions between neighbouring benzene rings, and the intermolecular plane-to-plane distances are 3.488 (2) and 3.841 (3) Å along the b and c axes, respectively. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link each molecule to two others, forming an infinite three-dimensional supramolecular structure.
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