Bis[4-(2-hydroxy­benzyl­amino)phen­yl] ether

Ya-Nan Guo; Chun-Hua Ge; Xiang-Dong Zhang; Xiao-Yan Zhang; Qi-Tao Liu

doi:10.1107/S1600536807061740

. 2008 Jan 23;64(Pt 2):o505. doi: 10.1107/S1600536807061740

Bis[4-(2-hydroxybenzylamino)phenyl] ether

Ya-Nan Guo ^a, Chun-Hua Ge ^a,^*, Xiang-Dong Zhang ^a, Xiao-Yan Zhang ^a, Qi-Tao Liu ^a

PMCID: PMC2960403 PMID: 21201525

Abstract

The title compound, C₂₆H₂₄N₂O₃, was synthesized by reduction of the corresponding Schiff base. The molecule does not possess crystallographic or non-crystallographic symmetry. The dihedral angle between the oxygen-bridged benzene rings is 67.98 (8)°. Both hydroxyl groups are involved in O—H⋯O intramolecular hydrogen bonding. The molecules are linked into a two-dimensional network parallel to the (010) plane by N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Ge, Zhang, Zhang, Guan et al. (2003 ▶); Ge, Zhang, Zhang, Guo et al. (2003 ▶).

Experimental

Crystal data

C₂₆H₂₄N₂O₃
M _r = 412.47
Monoclinic,
a = 5.8241 (5) Å
b = 43.960 (4) Å
c = 8.2874 (7) Å
β = 92.287 (1)°
V = 2120.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 (2) K
0.30 × 0.26 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.971, T _max = 0.982
11851 measured reflections
4170 independent reflections
2737 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.095
S = 0.93
4170 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a ▶); molecular graphics: SHELXTL (Sheldrick, 1997b ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061740/ci2520sup1.cif

e-64-0o505-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061740/ci2520Isup2.hkl

e-64-0o505-Isup2.hkl^{(204.4KB, hkl)}

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
O1—H1⋯N1	0.90 (2)	1.80 (2)	2.628 (2)	152 (2)
O3—H3⋯N2	0.94 (3)	1.82 (3)	2.670 (2)	150 (2)
N1—H1B⋯O3ⁱ	0.88 (2)	2.00 (2)	2.876 (2)	179 (2)
N2—H2B⋯O1ⁱⁱ	0.88 (2)	2.03 (2)	2.914 (2)	176 (2)

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

Acknowledgments

This work was supported by the Natural Science Foundation of the Education Bureau of Liaoning Province (grant No. 05 L159).

supplementary crystallographic information

Comment

The title compound has amino and hydroxyl groups which are good donor and acceptor for hydrogen bonding (Fig. 1). There are rigid phenyl rings and flexible methylene units in the same molecule which is similar to the ligands reported by Ge, Zhang, Zhang, Guan et al. (2003) and Ge, Zhang, Zhang, Guo et al. (2003). The molecule can be used as a semi-rigid ligand for metal complex formation or as a host for small molecule.

The dihedral angles formed by the C1—C6 (A), C8—C13 (B), C14—C19 (C) and C21—C26 (D) benzene rings are: A/B 66.36 (8)°, B/C 67.98 (8)° and C/D 67.68 (8)°. Both hydroxyl groups in the title molecule are involved in O—H···O intramolecular hydrogen bonding (Table 1). The molecules are linked into a two-dimensional network parallel to the (0 1 0) plane by N—H···O hydrogen bonds (Fig. 2).

Experimental

A solution of 4,4'-diaminodiphenyl ether (0.1 mol) in ethanol (50 ml) was added dropwise to a solution of salicylaldehyde (0.21 mol) in ethanol (50 ml). The mixture was stirred for 4 h. The resulting solution was filtered to obtain a Schiff base, and it was dried. The title compound was obtained by the reaction of the Schiff base (0.05 mol) with a solution of NaBH₄ (0.4 mol) in ethanol (30 ml). Removal of the solvent under vacuum gave a white solid. Single crystals of the title compound were obtained by evaporating a solution of above-mentioned solid (0.2 mmol) in ethanol-water (30 ml, 2:1 v/v).