2-[1-(3-Amino­phenyl­imino)­eth­yl]phenol

Anita Blagus; Branko Kaitner

doi:10.1107/S1600536811017624

. 2011 May 14;67(Pt 6):o1423. doi: 10.1107/S1600536811017624

2-[1-(3-Aminophenylimino)ethyl]phenol

Anita Blagus ^a,^*, Branko Kaitner ^b

PMCID: PMC3120413 PMID: 21754803

Abstract

The title compound, C₁₄H₁₄N₂O, exists as the enol–imine tautomer. A strong intramolecular hydrogen bond between O and N atoms forms a six-membered ring with an S(6) graph-set motif, which is approximately coplanar with the phenol ring, the interplanar angle being 3.4 (3)°. In the crystal, intermolecular C—H⋯O hydrogen bonds and N—H⋯π interactions link the molecules into infinite chains along [100].

Related literature

For background to Schiff base compounds, see: Blagus & Kaitner (2007 ▶); Blagus et al. (2010 ▶). For the photochromic and thermochromic characteristics of Schiff bases, see: Hadjoudis & Mavridis (2004 ▶). For graph-set notation of hydrogen bonds, see Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₄N₂O
M _r = 226.27
Orthorhombic,
a = 9.0625 (2) Å
b = 5.5777 (2) Å
c = 23.2349 (6) Å
V = 1174.48 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.6 × 0.5 × 0.4 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer
6829 measured reflections
1317 independent reflections
1145 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.087
S = 1.10
1317 reflections
165 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2003 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2003 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶), PARST97 (Nardelli, 1995 ▶) and Mercury (Macrae et al., 2006 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017624/fy2009sup1.cif

e-67-o1423-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017624/fy2009Isup3.hkl

e-67-o1423-Isup3.hkl^{(65.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811017624/fy2009Isup3.cml

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

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

Cg is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	1.04 (4)	1.59 (4)	2.540 (2)	150 (3)
C8—H8B⋯O1ⁱ	0.96	2.71	3.243 (3)	116
N2—H1N2⋯Cgⁱ	0.90 (4)	2.71 (4)	3.457 (3)	142 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support by the Ministry of Science, Education and Sport of the Republic of Croatia is gratefully acknowledged (grant No. 119–1193079–3069).

supplementary crystallographic information

Comment

Schiff bases are some of the most widely used chelating ligands in the field of metal-organic coordination chemistry (Blagus et al., 2010). The Schiff bases derived from ortho hydroxy aldehydes or ketons and aromatic diamines often have photochromic and thermochromic characteristics (Hadjoudis & Mavridis 2004). In this work we report the preparation and the crystal and molecular structure of a novel ketimine Schiff base 2-[1-(3-aminophenylimino)ethyl]phenol (Scheme 1).

The presence of intramolecular O1–H···N1 hydrogen bond [2.540 (2) Å] shows unequivocally that the molecular conformation of compound (1) in the crystalline state is in the enol-imino form. As shown in Figure 2, the Schiff base molecules link mutually in an one-dimensional chain forming a graph-set motif C(5) in the notation of Bernstein et al., (1995) along the [100] direction through a C–H···O [3.243 (3) Å] intermolecular hydrogen bond. Another intermolecular connection between the same neighbouring molecules forms through the terminal primary N2-amino group N–H···π interaction [3.457 (3) Å; π refers to the C9—C14 aromatic system centroid). All bond lengths are within the standard values (Allen et al., 1987) and are comparable with the similar ketimine Schiff bases as cited above (Blagus & Kaitner, 2007).

Experimental

The title compound was prepared by refluxing a methanolic solution of m-phenylendiamine (540 mg, 5 mmol) and 2-hydroxyacetophenone (1.25 ml, 10 mmol) for 4 h at the temperature of 80 °C. The water formed during the reaction was removed by a Dean-Stark trap. After cooling, the brown solid precipitate was filtered. Diffraction quality crystals were obtained by slow evaporation from ether solution.