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

Rakesh S Sancheti; Amol G Dikundwar; Ratnamala S Bendre

doi:10.1107/S1600536811020952

. 2011 Jun 11;67(Pt 7):o1605. doi: 10.1107/S1600536811020952

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

Rakesh S Sancheti ^a, Amol G Dikundwar ^b, Ratnamala S Bendre ^a,^*

PMCID: PMC3152006 PMID: 21837013

Abstract

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.

Related literature

For the synthesis of the title compound, see: Rossi et al. (2005 ▶). For related structures, see: Butcher et al. (2005 ▶, 2007 ▶). For the activities of related metal complexes, see: Ruiz et al. (2010 ▶); Yajima et al. (2002 ▶); Sarkar et al. (2006 ▶); Neves et al. (1999 ▶).

Experimental

Crystal data

C₂₆H₃₂N₂O₃
M _r = 420.54
Triclinic,
a = 8.0940 (6) Å
b = 11.3611 (7) Å
c = 13.7625 (10) Å
α = 79.944 (6)°
β = 82.915 (6)°
γ = 71.745 (6)°
V = 1180.21 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.30 × 0.30 × 0.20 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.977, T _max = 0.985
23864 measured reflections
4083 independent reflections
3232 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.163
S = 1.06
4083 reflections
285 parameters
H-atom parameters constrained
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020952/gk2373sup1.cif

e-67-o1605-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020952/gk2373Isup2.hkl

e-67-o1605-Isup2.hkl^{(196KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020952/gk2373Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N2ⁱ	0.82	2.09	2.897 (2)	166
O3—H3⋯N1	0.82	1.99	2.721 (2)	147
C14—H14A⋯O2	0.97	2.51	3.199 (3)	128
C23—H23⋯O3ⁱⁱ	0.93	2.47	3.114 (3)	127

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the DST, India, for funding under DST-FIST (Level II) for the X-ray diffraction facility at SSCU, Indian Institute of Science, Bangalore.

supplementary crystallographic information

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 N₂O₂ 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.