(E)-1-[(3-Bromo­phen­yl)imino­meth­yl]naphthalen-2-ol

Tufan Akbal; Ayşen Ağar Alaman; Sümeyye Gümüş; Ahmet Erdönmez

doi:10.1107/S1600536812034824

. 2012 Aug 25;68(Pt 9):o2779. doi: 10.1107/S1600536812034824

(E)-1-[(3-Bromophenyl)iminomethyl]naphthalen-2-ol

Tufan Akbal ^a,^*, Ayşen Ağar Alaman ^b, Sümeyye Gümüş ^b, Ahmet Erdönmez ^a

PMCID: PMC3435811 PMID: 22969657

Abstract

The title compound, C₁₇H₁₂BrNO, exists in an enol–imine form and the molecular structure features an intramolecular O—H⋯N hydrogen bond. The dihedral angle between the benzene ring and the naphthalene ring system is 17.27 (15)°.

Related literature

For general background to and applications of Schiff bases, see: Garnovski et al. (1993 ▶); Hamilton et al. (1987 ▶); Pyrz et al. (1985 ▶); Costamagna et al. (1992 ▶). For a related structure, see: Ünver et al. (2000 ▶).

Experimental

Crystal data

C₁₇H₁₂BrNO
M _r = 326.19
Monoclinic,
a = 31.3965 (19) Å
b = 4.8657 (2) Å
c = 19.0124 (11) Å
β = 107.772 (4)°
V = 2765.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 2.97 mm⁻¹
T = 296 K
0.80 × 0.36 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.421, T _max = 0.680
14469 measured reflections
2706 independent reflections
1992 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.117
S = 1.02
2706 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.47 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: WinGX (Farrugia, 1999 ▶) and 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034824/is5182sup1.cif

e-68-o2779-sup1.cif^{(23.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034824/is5182Isup2.hkl

e-68-o2779-Isup2.hkl^{(130.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034824/is5182Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812034824/is5182Isup4.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
O1—H1A⋯N1	0.82	1.82	2.548 (4)	147

Open in a new tab

Acknowledgments

The authors thank the Ondokuz Mayis University Research Fund for financial support of this project.

supplementary crystallographic information

Comment

Schiff bases from 2-hydroxy-1-naphthaldehyde have often been used as chelating ligands in the field coordination chemistry (Garnovski et al., 1993). The Schiff base complexes have also been used in catalytic reactions (Hamilton et al., 1987) and used as models for biological systems (Pyrz et al., 1985; Costamagna et al., 1992). There are two types of intramolecular hydrogen bonds in Schiff bases, namely keto-amine (N—H···O) and enol-imine (N···H—O) tautomeric forms.

The present X-ray investigation shows that the title compound, (I), prefers the enol-imine tautomeric form rather than the keto-amine tautomeric form (Fig. 1). The C9—O1 and C7—N1 bond lengths verify the enol-imine tautomeric form; these distances agree with the literature [1.310 (8) and 1.319 (6) Å; Ünver et al., 2000], which also shows the enol-imine tautomeric form. The C6—Br1 bond length in (I) is also in a good agreement with the corresponding distance in the literature [1.904 (2) Å; Ünver et al., 2000]. The molecule is non-planar. The dihedral angle between the two Schiff base moieties (C1–C6/N1) and (C7–C13/O1) is 16.27 (12)°. A view of the crystal packing of the title compound is shown in Fig. 2. π–π interactions between the centroids of the Cg1 and Cg2 rings [distance between ring centroids = 4.6002 (19) Å], and the Cg2 and Cg3 rings [distance between ring centroids = 4.805 (2) Å], stack the molecules along the b-axis. Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C8–C13 and C12–C17 rings, respectively.

Experimental

The compound (E)-1-[(3-bromophenyllimino)methyl]naphthalen-2-ol was prepared by refluxing a mixture of a solution containing 2-hydroxy-1-naphthaldehyde (17.2 mg, 0.100 mmol) in 30 ml absolute ethanol and a solution containing 3-bromoaniline (17.2 mg, 0.100 mmol) in 20 ml absolute ethanol. The reaction mixture was stirred for 4 h under reflux. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield 72%; m.p. 398–400 K).