2-{[{2-Hydroxy-3-[2-methyl-5-(propan-2-yl)phenoxy]propyl}(pyridin-2-ylmethyl)amino]methyl}phenol

In the title racemic compound, C26H32N2O3, an intramolecular O—H⋯N hydrogen bond is formed between the phenolic OH group and the tertiary amine N atom. Another O—H⋯N hydrogen bond that is formed between the OH group and the pyridine N atom links the molecules into a polymeric chain extending along the a axis. The structure is further stabilized by intramolecular and intermolecular C—H⋯O interactions.

In the title racemic compound, C 26 H 32 N 2 O 3 , an intramolecular O-HÁ Á ÁN hydrogen bond is formed between the phenolic OH group and the tertiary amine N atom. Another O-HÁ Á ÁN hydrogen bond that is formed between the OH group and the pyridine N atom links the molecules into a polymeric chain extending along the a axis. The structure is further stabilized by intramolecular and intermolecular C-HÁ Á ÁO interactions.

Comment
The chemistry of asymmetric polydentate ligands evokes interest, mainly towards the synthesis of biologically active coordination compounds. DNA metallointercalators have received considerable attention over the past few years because of their possible uses as new therapeutic agents and also for their interesting photochemical properties (Ruiz et al., 2010;Yajima et al., 2002;Sarkar et al., 2006). There are several reports on copper complexes of the asymmetrical ligands exhibiting important biological activities such as genomic and plasmid DNA cleavage and cytotoxic activity (Neves et al., 1999;Rossi et al., 2005).
The title compound was synthesized for preparation of metal complexes which would act as chemical nucleases. The ligand coordinates with a metal ion through its N 2 O 2 donor set along with an additional halide ligand to form a complex with distorted trigonal bipyramidal geometry. The molecular conformation of the ligand is nonplanar with O-H···N and C-H···O intramolecular hydrogen bonds, both forming the six-membered rings (Fig. 1, Table 1). Packing of the molecules is mainly guided by the intermolecular O-H···N hydrogen bonds connecting the 1-(5-isopropyl-2-methylphenoxy)propan-2-ol fragment of one molecule to the pyridine fragment of the other.

Experimental
The title compound was synthesized by the reaction of 2-[(5-isopropyl-2-methylphenoxy)methyl]oxirane (5.8 mmol, 1.20 g) with N-(2-hydroxybenzyl)-N-(2-pyridylmethyl)amine (5.8 mmol, 1.23 g) in methanol under reflux condition at 70°C for 8 h. The reaction mixture was cooled, filtered and the precipitated product was washed with cold methanol in order to remove the impurities (yield 66%, m.p. 407K). Crystals suitable for X-ray diffraction were obtained by slow evaporation of the saturated solution in acetonitrile at room temperature.

Refinement
All H atoms were positioned geometrically (C-H = 0.93-0.97 Å, O-H = 0.82 Å) and refined using a riding model with The high residual peak of 0.99 e Å -3 observed in a difference map was located at a distance of 1.05 Å from C12 and it may represent O atom of the OH group of the opposite enantiomer located at the same site in crystal. No reasonable model of the disorder could be obtained as the occupancy of the minor enantiomer should be only a few percent, with a significant overlap of the atomic positions. sup-2 Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å a = 8.0940 (6) Å Cell parameters from 23864 reflections b = 11.3611 (7) Å θ = 2.6-25.0°c = 13.7625 (10) Å µ = 0.08 mm −1 α = 79.944 (6)°T = 120 K β = 82.915 (6) supplementary materials sup-9