(E)-3-[(4-Diethyl­amino-2-hydroxy­benzyl­idene)amino]benzonitrile

Jian-Cheng Zhou; Zheng-Yun Zhang; Nai-Xu Li; Chuan-Ming Zhang

doi:10.1107/S1600536809050144

. 2009 Nov 28;65(Pt 12):o3251. doi: 10.1107/S1600536809050144

(E)-3-[(4-Diethylamino-2-hydroxybenzylidene)amino]benzonitrile

Jian-Cheng Zhou ^a,^b,^*, Zheng-Yun Zhang ^a, Nai-Xu Li ^a, Chuan-Ming Zhang ^a

PMCID: PMC2972081 PMID: 21578949

Abstract

The molecule of the title compound, C₁₈H₁₉N₃O, displays a trans configuration with respect to the C=N double bond. There is a strong intramolecular O—H⋯N hydrogen-bonding interaction between the hydroxy group and imine N atom. The dihedral angle between the aromatic rings is 30.35 (8)°. The crystal packing is stabilized by O—H⋯N links.

Related literature

For the properties of Schiff bases compounds, see: Zhou et al. (2000 ▶); Sriram et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-65-o3251-scheme1.jpg

Experimental

Crystal data

C₁₈H₁₉N₃O
M _r = 293.36
Triclinic,
a = 8.411 (6) Å
b = 8.519 (6) Å
c = 12.906 (9) Å
α = 74.17 (4)°
β = 79.00 (4)°
γ = 64.65 (2)°
V = 801.1 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.10 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.092, T _max = 0.182
8686 measured reflections
3620 independent reflections
2592 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.159
S = 1.09
3620 reflections
203 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 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/S1600536809050144/bx2250sup1.cif

e-65-o3251-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050144/bx2250Isup2.hkl

e-65-o3251-Isup2.hkl^{(177.5KB, 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	0.98 (3)	1.70 (3)	2.607 (3)	153 (2)
C16—H16A⋯O1ⁱ	0.93	2.60	3.504 (3)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported financially by the Jiangsu Provincial Key Laboratory of Pulp and Paper Science and Technology Foundation (No. 200813).

supplementary crystallographic information

Comment

Schiff bases compounds attract great interest in many fields of chemistry and biochemistry, primarily due to significant pharmacological activities, e.g. anticancer (Zhou et al., 2000), anti-HIV (Sriram et al., 2006). In addition, Schiff base compounds play important role in the development of coordination chemistry related to magnetism and catalysis. As a continue of my works, we here report the synthesis and crystal structure of the title compound, (I).

The molecular structure of (I) of the title compound is shown in Fig. 1. All the bond lengths and angles in the molecules are in the range of normal values (Allen et al., 1987). The molecule displays a trans configuration about the central C11=N2 bond and adopts the phenol-imine tautomeric form, with a strong intramolecular O—H···N hydrogen bonding interaction (Table 1). The dihedral angle between the mean planes of the two aromatic rings is 30.35 (8) ° indicating that the Schiff-base ligand adopts a non-planar conformation. In addition, two methyl groups are positioned to the opposite direction respectively relative to the plane of the adjacent benzene ring. The crystal packing is stabilized by van der Waals interactions.

Experimental

(E)-3-(4-(diethylamino)-2-hydroxybenzylideneamino)benzonitrile was prepared by reflux of a solution mixture containing 4-(diethylamino)-2-hydroxybenzaldehyde (0.996 g, 5 mmol) in ethanol (20 ml) and a solution containing 3-aminobenzonitrile (0.590 g, 5 mmol) in methanol (20 ml). The reaction mixture was stirred for 6 h under reflux, and then cooled to room temperature slowly. The resulting yellow precipitate was filtered off and the crystals of the title compound suitable for X-ray analysis were obtained from acetonitrile solution by slow evaporation