N′-(2-Hydroxy­naphthyl­idene)-4-methoxy­benzo­hydrazide

Chun-Bao Tang

doi:10.1107/S1600536808008076

. 2008 Mar 29;64(Pt 4):o768. doi: 10.1107/S1600536808008076

N′-(2-Hydroxynaphthylidene)-4-methoxybenzohydrazide

Chun-Bao Tang ^a,^*

PMCID: PMC2960934 PMID: 21202155

Abstract

The title Schiff base compound, C₁₉H₁₆N₂O₃, was derived from the condensation reaction of 2-hydroxy-1-naphthylaldehyde with 4-methoxybenzohydrazide. The dihedral angle between the benzene ring and the naphthyl ring system is 6.8 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O intermolecular hydrogen bonds, forming chains running along the c axis.

Related literature

For related structures, see: Tang (2006 ▶, 2007a ▶,b ▶,c ▶,d ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₁₆N₂O₃
M _r = 320.34
Monoclinic,
a = 11.159 (2) Å
b = 15.790 (3) Å
c = 8.8300 (18) Å
β = 91.70 (3)°
V = 1555.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.32 × 0.32 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.971, T _max = 0.972
13232 measured reflections
3550 independent reflections
2161 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.136
S = 1.04
3550 reflections
222 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808008076/sj2478sup1.cif

e-64-0o768-sup1.cif^{(16.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008076/sj2478Isup2.hkl

e-64-0o768-Isup2.hkl^{(174.1KB, 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—H1⋯N1	0.82	1.86	2.582 (2)	146
N2—H2⋯O2ⁱ	0.904 (9)	1.957 (12)	2.834 (2)	163 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support from the Jiaying University Research Fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Recently, the author has reported the structures of several Schiff base compounds (Tang, 2006, 2007a,b,c,d) and, in continuation of work in this area, reports herein the structure of the title compound, (I), Fig. 1, a new Schiff base compound.

In the title compound (Fig. 1), the dihedral angle between the benzene ring and the naphtyl ring is 6.8 (2)°. The torsion angles C1—C11—N1—N2, C11—N1—N2—C12, and N1—N2—C12—C13 are 1.3 (2), 17.0 (2), and 1.5 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through N—H···O intermolecular hydrogen bonds (Table 1), forming chains running along the c axis (Fig. 2).

Experimental

2-Hydroxy-1-naphtylaldehyde (0.1 mmol, 17.2 mg) and 4-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were dissolved in an ethanol solution (20 ml). The mixture was stirred at reflux for 10 min to give a clear colorless solution. Colorless needle-like crystals of the compound were formed by slow evaporation of the solvent over several days.