(E)-2-[(2-Ethyl­phen­yl)imino­meth­yl]-6-methoxy­phenol

Serap Yazıcı; Çiğdem Albayrak; İsmail Gümrükçüoğlu; İsmet Şenel; Orhan Büyükgüngör

doi:10.1107/S1600536809055573

. 2010 Jan 9;66(Pt 2):o287. doi: 10.1107/S1600536809055573

(E)-2-[(2-Ethylphenyl)iminomethyl]-6-methoxyphenol

Serap Yazıcı ^a,^*, Çiğdem Albayrak ^b, İsmail Gümrükçüoğlu ^c, İsmet Şenel ^a, Orhan Büyükgüngör ^a

PMCID: PMC2979675 PMID: 21579722

Abstract

The molecule of the title compound, C₁₆H₁₇NO₂, adopts the phenol–imine tautomeric form with a strong intramolecular O—H⋯N hydrogen bond and an E conformation with respect to the azomethine C=N bond. The dihedral angle between the aromatic rings is 21.23 (9)°. The ethyl group is disordered over two orientations with occupancies of 0.598 (6) and 0.402 (6). In the crystal, the molecules are linked into chains along the b axis by C—H⋯π interactions.

Related literature

For general background to o-hydroxy Schiff bases, see: Stewart & Lingafelter (1959 ▶); Calligaris et al. (1972 ▶); Maslen & Waters (1975 ▶). For the photochromic and thermochromic characteristics of Schiff base compounds, see: Cohen et al. (1964 ▶); Moustakali-Mavridis et al. (1980 ▶); Hadjoudis et al. (1987 ▶); Xu et al. (1994 ▶). For a related structure, see: Yüce et al. (2004 ▶).

Experimental

Crystal data

C₁₆H₁₇NO₂
M _r = 255.31
Monoclinic,
a = 18.2379 (7) Å
b = 5.2044 (2) Å
c = 15.0950 (7) Å
β = 113.788 (3)°
V = 1311.05 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.58 × 0.39 × 0.08 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.961, T _max = 0.993
18335 measured reflections
3014 independent reflections
2353 reflections with I > 2σ(I)
R _int = 0.072

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.115
S = 1.03
3014 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055573/ci5005sup1.cif

e-66-0o287-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055573/ci5005Isup2.hkl

e-66-0o287-Isup2.hkl^{(144.9KB, hkl)}

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

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

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.98 (2)	1.68 (2)	2.6023 (15)	156 (2)
C14—H14c⋯Cg1ⁱ	0.96	2.83	3.6241 (18)	141

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

supplementary crystallographic information

Comment

o-Hydroxy Schiff bases derived from the reaction of o-hydroxyaldehydes with aniline have been examined extensively (Steward & Lingafelter, 1959; Calligaris et al., 1972; Maslen & Waters, 1975). Schiff base compounds display interesting photochromic and thermochromic features and can be classified in terms of these (Cohen et al., 1964; Moustakali-Mavridis et al., 1980; Hadjoudis et al., 1987). Photo- and thermochromism arise via H atom transfer from the hydroxy O atom to the N atom (Hadjoudis et al., 1987; Xu et al., 1994).

The molecule of the title compound (Fig. 1) exists in the phenol-imine form which is confirmed by C13—O1 and C7—N1 bond distances. These distances agree with the corresponding distances in 1-{4-[(2-hydroxybenzylidene)amino]phenyl}ethanone, a related structure [C—O = 1.3500 (17) and C—N = 1.2772 (16) Å; Yüce et al., 2004].

The title molecule is not planar; the dihedral angle between the two benzene rings is 21.23 (9)°. An intramolecular O1—H1···N1 hydrogen bond (Fig. 1) generates an S(6) ring-motif.

The crystal structure is stabilized by weak C—H···π interactions involving H14C and C8–C13 ring (Fig. 2).

Experimental

A solution of 3-methoxysalicylaldehyde (0.5 g 3.3 mmol) in ethanol (20 ml) was added to a solution of 2-ethylaniline (0.4 g 3.3 mmol) in ethanol (20 ml). The reaction mixture was stirred for 1 h under reflux. Single crystals of the title compound were obtained by slow evaporation of an ethanol solution (yield 72%, m.p. 339-340 K).