3-Hydr­oxy-N′-(2-methoxy­benzyl­idene)-2-naphthohydrazide

Yu-Mei Hao

doi:10.1107/S1600536809043086

. 2009 Nov 4;65(Pt 12):o2990. doi: 10.1107/S1600536809043086

3-Hydroxy-N′-(2-methoxybenzylidene)-2-naphthohydrazide

Yu-Mei Hao ^a,^*

PMCID: PMC2971856 PMID: 21578730

Abstract

In the title Schiff base compound, C₁₉H₁₆N₂O₃, the dihedral angle between the mean planes of the benzene ring and the naphthyl ring system is 0.8 (2)°. The mean plane of the hydrazide group forms dihedral angles of 2.0 (2) and 2.2 (2)°, respectively, with the mean planes of the benzene ring and the naphthyl ring system. A strong intramolecular N—H⋯O hydrogen bond is present. In the crystal, intermolecular O—H⋯O hydrogen bonds form chains along the c axis and help to provide stability in the crystal packing.

Related literature

For the pharmaceutical and medicinal activities of Schiff bases, see: Dao et al. (2000 ▶); Sriram et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For the coordination chemistry of Schiff bases, see: Ali et al. (2008 ▶); Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For the crystal structures of Schiff base compounds, see: Fun et al. (2009 ▶); Nadeem et al. (2009 ▶); Eltayeb et al. (2008 ▶); Hao (2009a ▶,b ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-65-o2990-scheme1.jpg

Experimental

Crystal data

C₁₉H₁₆N₂O₃
M _r = 320.34
Monoclinic,
a = 7.4990 (6) Å
b = 15.4256 (13) Å
c = 13.3903 (12) Å
β = 96.709 (4)°
V = 1538.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.983, T _max = 0.984
9323 measured reflections
3349 independent reflections
2520 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.119
S = 1.04
3349 reflections
223 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536809043086/jj2010sup1.cif

e-65-o2990-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043086/jj2010Isup2.hkl

e-65-o2990-Isup2.hkl^{(164.3KB, 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—H2⋯O3	0.892 (9)	1.929 (14)	2.6613 (14)	138.3 (16)
O3—H3⋯O2ⁱ	0.82	1.86	2.6689 (13)	167

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Schiff base compounds, important to the pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006), have been used as versatile ligands in a variety of coordination chemistry applications (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). A number of contributions to these areas have been recently reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). With our continued interest in the structural chararcterization of these compounds (Hao, 2009a,b) the title compound, C₁₉H₁₆N₂O₃, (I), is reported.

In the title compound,(I), the mean plane of the hydrazide group, O2/C9/N2/N1/C8, forms dihedral angles of 2.0 (2) and 2.2 (2)°, with the mean planes of the benzene (C1–C6) and naphthyl rings (C10–C19), respectively (Fig. 1). The dihedral angle between the mean planes of the benzene and naphthyl rings is 0.9 (2)°, indicating the planarity of the molecule. All the bond lengths and angles are within normal values (Allen et al., 1987). Crystal packing is enhanced by strong intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (Table 1), forming infinite one-dimensional chains running along the c axis of the unit cell (Fig. 2).

Experimental

2-Methoxybenzaldehyde (0.1 mmol, 13.6 mg) and 3-hydroxy-2-naphthohydrazide (0.1 mmol) were refluxed in a 30 ml methanol solution for 30 min to give a clear colorless solution. Colorless block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.