N′-[(2-Methoxynaphthalen-1-yl)methyl­idene]-4-methyl­benzohydrazide

Xu-Feng Meng; Dong-Yue Wang; Jing-Jun Ma

doi:10.1107/S1600536811044291

. 2011 Oct 29;67(Pt 11):o3109. doi: 10.1107/S1600536811044291

N′-[(2-Methoxynaphthalen-1-yl)methylidene]-4-methylbenzohydrazide

Xu-Feng Meng ^a, Dong-Yue Wang ^a, Jing-Jun Ma ^a,^*

PMCID: PMC3247494 PMID: 22220112

Abstract

In the title compound, C₂₀H₁₈N₂O₂, the mean planes of the naphthyl system and the benzene ring form a dihedral angle of 88.48 (10)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) chains, which propagate along the b-axis direction.

Related literature

For the biological activity of benzohydrazide compounds, see: El-Sayed et al. (2011 ▶); Horiuchi et al. (2009 ▶). For coordination compounds of benzohydrazide compounds, see: El-Dissouky et al. (2010 ▶); Zhang et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the crystal structures of similar compounds, see: Suleiman Gwaram et al. (2010 ▶); Liu et al. (2011 ▶); Zhou et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₁₈N₂O₂
M _r = 318.36
Orthorhombic,
a = 26.738 (3) Å
b = 4.893 (2) Å
c = 12.735 (2) Å
V = 1666.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.984, T _max = 0.985
12400 measured reflections
3622 independent reflections
2579 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.100
S = 1.03
3622 reflections
222 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (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 datablock(s) I, global. DOI: 10.1107/S1600536811044291/hb6475sup1.cif

e-67-o3109-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044291/hb6475Isup2.hkl

e-67-o3109-Isup2.hkl^{(177.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811044291/hb6475Isup3.cml

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⋯O2ⁱ	0.91 (1)	1.99 (1)	2.882 (2)	168 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

This project was sponsored by the Natural Development Foundation of Hebei Province (B2011204051), the Development Foundation of the Department of Education of Hebei Province (2010137) and the Research Development Foundation of the Agricultural University of Hebei.

supplementary crystallographic information

Comment

Benzohydrazide compounds are well known for their biological activities (El-Sayed et al., 2011; Horiuchi et al., 2009). In addition, benzohydrazide compounds have also been used as versatile ligands in coordination chemistry (El-Dissouky et al., 2010, Zhang et al., 2010). As a contribution to a structural study on hydrazone compounds, we present here the crystal structure of the title compound, that was obtained as the product of the reaction of 2-methoxy-1-naphthaldehyde with 4-methylbenzohydrazide in methanol.

In the title compound, Fig. 1, the mean planes of the naphthyl ring and the benzene ring form a dihedral angle of 91.5 (3)°. The bond distances and angles are within normal ranges (Allen et al., 1987), and agree well with the corresponding bond distances and angles reported in closely related compounds (Suleiman Gwaram et al., 2010; Liu et al., 2011; Zhou et al., 2011).

In the crystal, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules to form chains which propagate along the b axis direction (Fig. 2).

Experimental

To a methanol solution (20 ml) of 5-bromosalicylaldehyde (0.1 mmol, 20.1 mg) and 4-nitrobenzohydrazide (0.1 mmol, 18.1 mg), a few drops of acetic acid were added. The mixture was refluxed for 1 h and then cooled to room temperature. The white crystalline solid was collected by filtration, washed with cold methanol and dried in air. Colourless blocks were obtained by slow evaporation of a methanol solution of the product in air.