(E)-N′-[(2-Hy­droxy-1-naphthalen-1-yl)methyl­idene]-3-methyl­benzohydrazide

Shi-Yong Liu; Shan-Shan Sun; Ting-Ting Zheng; Xiang-Lei Zheng; Xiao-Feng Zhao; Xiao-Fang Li

doi:10.1107/S1600536811010361

. 2011 Mar 26;67(Pt 4):o965. doi: 10.1107/S1600536811010361

(E)-N′-[(2-Hydroxy-1-naphthalen-1-yl)methylidene]-3-methylbenzohydrazide

Shi-Yong Liu ^a,^*, Shan-Shan Sun ^a, Ting-Ting Zheng ^a, Xiang-Lei Zheng ^a, Xiao-Feng Zhao ^a, Xiao-Fang Li ^b

PMCID: PMC3099761 PMID: 21754228

Abstract

In the title compound, C₁₉H₁₆N₂O₂, the benzene ring and naphthyl ring system are inclined at a dihedral angle of 16.1 (3)°. An intramolecular O—H⋯N hydrogen bond influences the molecular conformation. In the crystal, molecules are linked through N—H⋯O hydrogen bonds into chains running along the a axis.

Related literature

For the medicinal applications of hydrazone compounds, see: Hillmer et al. (2010 ▶); Raj et al. (2007 ▶). For hydrazones we have reported previously, see: Liu & You (2010 ▶); Liu & Wang (2010 ▶). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009 ▶). For related structures, see: Xu et al. (2009 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C₁₉H₁₆N₂O₂
M _r = 304.34
Monoclinic,
a = 7.1927 (11) Å
b = 31.042 (4) Å
c = 7.3557 (11) Å
β = 108.455 (2)°
V = 1557.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.983, T _max = 0.985
8247 measured reflections
3295 independent reflections
1736 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.166
S = 1.04
3295 reflections
214 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010361/sj5120sup1.cif

e-67-0o965-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010361/sj5120Isup2.hkl

e-67-0o965-Isup2.hkl^{(161.7KB, 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⋯O2ⁱ	0.90 (1)	2.00 (1)	2.869 (3)	163 (3)
O1—H1⋯N1	0.82	1.85	2.567 (3)	146

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Undergraduate Innovation Group Project of Zhejiang Province (project no. 2010R428015).

supplementary crystallographic information

Comment

Considerable attention has been focused on hydrazones and their medicinal applications (Hillmer et al., 2010; Raj et al., 2007). The crystal structures of such compounds are of particular interest (Vijayakumar et al., 2009). As a continuation of our work on similar compounds (Liu & You, 2010; Liu & Wang, 2010), we report herein the crystal structure of the title compound a new hydrazone.

The molecular structure of the title compound is shown in Fig. 1. The benzene ring and the naphthyl ring system are inclined at a dihedral angle of 16.1 (3) °. The dihedral angle between the C1—C10 benzene ring and the C13—C18 naphthyl ring is 16.1 (3)°. All the bond lengths are comparable to those observed in related structures (Xu et al., 2009; Shafiq et al., 2009) and those we reported previously.

In the crystal structure, molecules are linked through N–H···O hydrogen bonds, to form one-dimensional chains running along the a axis (Fig. 2 and Table 1).

Experimental

The title compound was prepared by the condensation reaction of 2-hydroxy-1-naphthaldehyde (0.05 mol, 8.6 g) and 3-methylbenzohydrazide (0.05 mol, 7.5 g) in anhydrous methanol (200 ml) at ambient temperature. Colourless block-shaped single crystals suitable for X-ray structural determination were obtained by slow evaporation of the solution for a period of a week.