2-[(2-Meth­oxy­benzyl­idene)amino]­phenol

M Aslam; I Anis; N Afza; M T Hussain; S Yousuf

doi:10.1107/S1600536812016224

. 2012 Apr 21;68(Pt 5):o1447. doi: 10.1107/S1600536812016224

2-[(2-Methoxybenzylidene)amino]phenol

M Aslam ^a,^b,^‡, I Anis ^b, N Afza ^a, M T Hussain ^c, S Yousuf ^d,^*

PMCID: PMC3344564 PMID: 22590326

Abstract

In the title compound, C₁₄H₁₃NO₂, the azomethine double bond adopts an E conformation and the benzene rings form a dihedral angle of 77.70 (7)°. In the crystal, molecules are linked by O—H⋯N and C—H⋯O hydrogen bonds and arranged in a zigzag fashion, forming infinite chains parallel to the c axis, resulting in a graph-set R ₂ ²(9) motif.

Related literature

For the biological activity of Schiff bases, see: Khan et al. (2009 ▶); Gerdemann et al. (2002 ▶); Samadhiya & Halve (2001 ▶). For a related structure, see: Liang et al. (2009 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₂
M _r = 227.25
Monoclinic,
a = 9.8709 (5) Å
b = 6.6606 (3) Å
c = 18.6128 (9) Å
β = 105.249 (1)°
V = 1180.63 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 273 K
0.49 × 0.17 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.959, T _max = 0.986
6660 measured reflections
2186 independent reflections
1680 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.100
S = 1.04
2186 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016224/pv2528sup1.cif

e-68-o1447-sup1.cif^{(17KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016224/pv2528Isup2.hkl

e-68-o1447-Isup2.hkl^{(107.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016224/pv2528Isup3.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—H2A⋯N1ⁱ	0.88 (2)	1.94 (2)	2.796 (2)	163 (2)
C10—H10A⋯O2ⁱ	0.93	2.56	3.269 (2)	133

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Symmetry code: (i) Inline graphic .

Acknowledgments

MA express his gratitude to the Pakistan Council of Scientific and Industrial Research Laboratories Complex, Karachi, the Department of Chemistry, University of Karachi and the H·E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for providing financial support, research facilities and X-ray diffraction facilities, respectively.

supplementary crystallographic information

Comment

Schiff base ligands have remained an imperative part of research due to their used as intermediates and precursors for the synthesis of a variety of organic compounds having a broad range of biological activities (Khan et al., 2009; Gerdemann et al., 2002; Samadhiya & Halve, 2001). The title compound was prepared as a part of our ongoing research on bioactive compounds.

In the title molecule (Fig. 1), the azomethine (C═N, 1.2729 (18) Å) double bond adopts an E configuration. The bond lengths and angles in the title compound are similar to the corresponding bond lenghts and bond angles reported in a closely related compound, 2-(2,3,4-trimethoxy-6-methylbenzylideneamino)phenol (Liang et al., 2009). The crystal structure is stabilized by O2—H2A···N1 and C1—H1B···O1 intermolecular hydrogen bonds resulting in chains of molecules lying parallel to the c-axis in a zig zag fashion (Fig. 2 and Tab. 1). The molecules lying about screw axis parallel to the c-axis form 9-membered rings due to hydrogen bonds in a motif with graph set R₂²(9) (Bernstein et al., 1995).

Experimental

A mixture of 2-methoxybenzaldehyde (0.01 mol, 1.36 g) and 2-aminophenol (0.01 mol, 1.09 g) in ethanol (50 ml) along with 3–4 drops of conc. H₂SO₄ was refluxed for 3 h at 343 K. After cooling, the mixture was concentrated to one third of its volume under reduced pressure. The concentrated reaction mixture was kept at room temperature and light yellow crystals were obtained after five days. The crystalline product was collected, washed with methanol and dried to afford the title compound in 79% yield. Slow evaporation of a methanol solution afforded light yellow crystals suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich.