(E)-2-(2,4-Dihydroxy­benzyl­ideneamino)benzonitrile

Ting Liu

doi:10.1107/S1600536809020182

. 2009 Jun 6;65(Pt 7):o1502. doi: 10.1107/S1600536809020182

(E)-2-(2,4-Dihydroxybenzylideneamino)benzonitrile

Ting Liu ^a,^*

PMCID: PMC2969512 PMID: 21582801

Abstract

The molecule of the title compound, C₁₄H₁₀N₂O₂, adopts the phenol–imine tautomeric form. The dihedral angle between the planes of the two benzene rings is 13.84 (13)°. A strong intramolecular O—H⋯N hydrogen-bonding interaction stabilizes the molecular conformation. In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular C—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the crystal structures of related compounds, see: Cheng et al. (2006 ▶); Xia et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₄H₁₀N₂O₂
M _r = 238.24
Monoclinic,
a = 13.322 (3) Å
b = 5.7505 (12) Å
c = 16.132 (3) Å
β = 108.97 (3)°
V = 1168.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.973, T _max = 0.979
11536 measured reflections
2683 independent reflections
1394 reflections with I > 2σ(I)
R _int = 0.073

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.153
S = 1.01
2683 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020182/rz2327sup1.cif

e-65-o1502-sup1.cif^{(14.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020182/rz2327Isup2.hkl

e-65-o1502-Isup2.hkl^{(131.8KB, 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—H1A⋯N2	0.95 (3)	1.70 (3)	2.581 (2)	152 (3)
O2—H2A⋯N1ⁱ	0.82	2.03	2.835 (3)	166
C11—H11A⋯O1ⁱ	0.93	2.56	3.386 (3)	148

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Schiff base compounds have attracted great attention and have been extensively investigated due to their important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures. Herein, the synthesis and crystal structure of the title compound is reported.

The molecular structure of the title compound is shown in Fig. 1. The Schiff-base molecule adopts a non-planar conformation, with the dihedral angle between the two aromatic rings of 13.84 (13)°, and displays a trans configuration with respect to the C8=N2 double bond. Bond lengths (Allen et al., 1987) and angles are normal and in good agreement with those reported for 5-chloro-2-(2-hydroxybenzylideneamino)benzonitrile (Cheng et al., 2006) and 2-(2-hydroxybenzylideneamino)benzonitrile (Xia et al., 2008). There is an strong intramolecular O—H···N hydrogen bond stabilizing the molecular conformation (Table 1). In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked into dimers by intermolecular C—H···O and O—H···N hydrogen bonds (Table 1).

Experimental

The title compound was prepared by refluxing a mixture of 2,4-dihydroxybenzaldehyde (0.552 g, 4 mmol) and 2-aminobenzonitrile (0.472 g, 4 mmol) in ethanol (20 ml). The reaction mixture was refluxed for 5 h under stirring, then cooled to room temperatureand and the resulting yellow precipitate was filtered off. Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.