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

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

doi:10.1107/S160053681101035X

. 2011 Mar 26;67(Pt 4):o964. doi: 10.1107/S160053681101035X

(E)-N′-[(2-Hydroxynaphthalen-1-yl)methylidene]-4-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: PMC3099921 PMID: 21754227

Abstract

In the title compound, C₁₉H₁₆N₂O₂, the benzene ring and the naphthyl ring system form a dihedral angle of 8.7 (3)° and an intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming C(4) chains propagating in [001].

Related literature

For hydrazones we have reported previously and background references, see: Liu & You (2010a ▶,b ▶,c ▶); Liu & Wang (2010a ▶,b ▶). For a related structure, see: Cao (2009 ▶).

Experimental

Crystal data

C₁₉H₁₆N₂O₂
M _r = 304.34
Monoclinic,
a = 11.014 (2) Å
b = 15.487 (2) Å
c = 9.150 (1) Å
β = 93.503 (3)°
V = 1557.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.20 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.983, T _max = 0.987
12464 measured reflections
3335 independent reflections
1515 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.192
S = 0.93
3335 reflections
213 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 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/S160053681101035X/hb5818sup1.cif

e-67-0o964-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101035X/hb5818Isup2.hkl

e-67-0o964-Isup2.hkl^{(163.6KB, 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)	2.02 (1)	2.897 (3)	164 (3)
O1—H1⋯N1	0.82	1.86	2.586 (3)	146

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

As a continuation of our structural studies of hydrazones (Liu & You, 2010a,b,c; Liu & Wang, 2010a,b), we report herein the crystal structure of the title compound, (I) (Fig. 1).

The dihedral angle between the C1—C10 benzene ring and the C13—C18 naphthyl ring is 8.7 (3)°. All the bond lengths are comparable to those observed in related structures (Cao, 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 c 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 4-methylbenzohydrazide (0.05 mol, 7.5 g) in anhydrous methanol (200 ml) at ambient temperature. Colourless blocks were obtained by slow evaporation of the solution for a period of a week.