N′-[4-(Dimethyl­amino)benzyl­idene]-3-hydr­oxy-2-naphthohydrazide

Hai-Tao Huang

doi:10.1107/S160053680900960X

. 2009 Mar 28;65(Pt 4):o892. doi: 10.1107/S160053680900960X

N′-[4-(Dimethylamino)benzylidene]-3-hydroxy-2-naphthohydrazide

Hai-Tao Huang ^a,^*

PMCID: PMC2969016 PMID: 21582600

Abstract

The title compound, C₂₀H₁₉N₃O₂, was obtained by the condensation of 4-(dimethylamino)benzaldehyde with 3-hydroxy-2-naphthohydrazide. The molecule is approximately planar, with an intramolecular N—H⋯O hydrogen bond involving the imino H atom and the hydroxy O atom. The dihedral angle between the benzene ring and the naphthyl mean plane is 2.72 (13)°. In the crystal structure, symmetry-related molecules are linked by intermolecular O—H⋯O hydrogen bonds, forming chains propagating in the c-axis direction.

Related literature

For background on compounds obtained by the condensation of aldehydes with benzohydrazides, see: Qiu & Zhao (2008 ▶); Yathirajan et al. (2007 ▶); Salhin et al. (2007 ▶). For informtaion concerning their biological properties, see: Küçükgüzel et al. (2003 ▶); Charkoudian et al. (2007 ▶). For similar structures, see: Fun et al. (2008 ▶); Liu & Li (2004 ▶); Lei et al. (2008 ▶). For bond-length values, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₀H₁₉N₃O₂
M _r = 333.38
Monoclinic,
a = 8.090 (2) Å
b = 15.798 (3) Å
c = 13.428 (3) Å
β = 98.978 (3)°
V = 1695.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.27 × 0.23 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.977, T _max = 0.981
13922 measured reflections
3670 independent reflections
1629 reflections with I > 2σ(I)
R _int = 0.075

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.190
S = 1.03
3670 reflections
232 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900960X/su2102sup1.cif

e-65-0o892-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900960X/su2102Isup2.hkl

e-65-0o892-Isup2.hkl^{(180KB, 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
N2—H2B⋯O2	0.898 (10)	1.90 (2)	2.644 (3)	139 (2)
O2—H2⋯O1ⁱ	0.82	1.85	2.651 (3)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by Qiqihar Medical University, China.

supplementary crystallographic information

Comment

In recent years compounds derived from the condensation of aldehydes with benzohydrazides have been widely investigated, either for their structures (Qiu & Zhao, 2008; Yathirajan et al., 2007; Salhin et al., 2007) or for their biological properties (Küçükgüzel et al., 2003); Charkoudian et al., 2007). The author reports herein the crystal structure of the title compound, obtained by the condensation of 4-dimethylaminobenzaldehyde with 3-hydroxy-2-naphthohydrazide.

The molecular structure of the title compound is illustrated in Fig. 1. The bond lengths are within normal values (Allen et al., 1987), and are comparable to the values in similar compounds (Fun et al., 2008; Liu & Li, 2004; Lei et al., 2008). The molecule is approximately coplanar, with the dihedral angle between the benzene ring and the naphthyl mean-plane being 2.72 (13)°. There is an intramolecular N-H···O hydrogen bond, involving the imino H-atom and the hydroxyl O-atom (Table 1).

In the crystal structure symmetry related molecules are linked via intermolecular O–H···O hydrogen bonds to form one-dimensional chains propagating in the c direction (Fig. 2 and Table 1).

Experimental

The title compound was prepared by the condensation of 4-dimethylaminobenzaldehyde (0.1 mol) and 3-hydroxy-2-naphthohydrazide (0.1 mmol) in ethanol (20 ml). The excess ethanol was removed by distillation. The colorless solid obtained was filtered and washed with ethanol. Single crystals, suitable for X-ray diffraction, were obtained on slow evaporation of a solution of the title compound in ethanol.