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

Xiao-Yan Li

doi:10.1107/S1600536811038153

. 2011 Sep 30;67(Pt 10):o2713. doi: 10.1107/S1600536811038153

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

Xiao-Yan Li ^a,^*

PMCID: PMC3201446 PMID: 22065731

Abstract

There are three independent molecules in the asymmetric unit of the title compound, C₁₉H₁₆N₂O₃, in which the dihedral angles between the naphthalene ring system and the benzene ring are 7.52 (16), 18.15 (18), and 13.9 (2)°. All the molecules exist in the trans configuration with respect to the methylidene units. In each molecule there is one O—H⋯N and one N—H⋯O intramolecular hydrogen bond. In the crystal, two of the molecules are linked via a bifurcated N—H⋯(O,O) hydrogen bond. All three molecules are further linked via C—H⋯O interactions.

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶); Li (2011a ▶). For the crystal structures of similar compounds reported recently by the author, see: Li (2011b ▶,c ▶).

Experimental

Crystal data

C₁₉H₁₆N₂O₃
M _r = 320.34
Triclinic,
a = 12.2266 (19) Å
b = 14.212 (3) Å
c = 15.805 (2) Å
α = 107.507 (3)°
β = 108.475 (3)°
γ = 95.885 (3)°
V = 2423.9 (7) Å³
Z = 6
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.23 × 0.23 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.980, T _max = 0.981
20059 measured reflections
10353 independent reflections
3438 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.184
S = 0.94
10353 reflections
666 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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) global, I. DOI: 10.1107/S1600536811038153/su2316sup1.cif

e-67-o2713-sup1.cif^{(30.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038153/su2316Isup2.hkl

e-67-o2713-Isup2.hkl^{(506.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038153/su2316Isup3.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
O1—H1⋯N1	0.82	1.84	2.556 (3)	145
N2—H2⋯O3	0.91 (1)	1.94 (2)	2.622 (3)	131 (3)
N2—H2⋯O8ⁱ	0.91 (1)	2.41 (2)	3.094 (4)	132 (2)
O4—H4⋯N3	0.86 (1)	1.82 (2)	2.538 (4)	141 (3)
N4—H4B⋯O6	0.91 (1)	1.95 (2)	2.647 (4)	132 (3)
O7—H7⋯N5	0.82	1.80	2.517 (4)	146
N6—H6A⋯O9	0.89 (1)	1.89 (2)	2.621 (4)	138 (3)
C11—H11⋯O8ⁱ	0.93	2.46	3.122 (4)	129
C38—H38B⋯O2ⁱⁱ	0.96	2.35	3.090 (5)	133
C57—H57B⋯O4ⁱⁱⁱ	0.96	2.56	3.435 (5)	151

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The author is grateful to the Zibo Vocational Institute for supporting this work.

supplementary crystallographic information

Comment

In the last few years, hydrazones have attracted much attention for their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b), the author reports herein on the crystal structure of the new title hydrazone compound.

In the asymmetric unit of the title compound there are three (A, B and C) independent molecules (Fig. 1). The bond distances and angles are comparable to those observed in similar compounds (Li, 2011b,c). The dihedral angles between the naphthalene and the benzene rings in the three molecules are 7.52 (16), 18.15 (18), and 13.9 (2)°, for molecules A, B and C, respectively. All the molecules exist in the trans configuration with respect to the methylidene units. In each molecule there is an O-H···N and a N-H···O intramolecular hydrogen bond (Table 1).

In the crystal the A and C molecules are linked by a bifurcated hydrogen bond involving the NH group of molecule A [N2-H2···O8] (Table 1). All three molecules are further linked to one another via C-H···O interactions (Table 1).

Experimental

A mixture of 2-methoxybenzhydrazide (0.166 g, 1 mmol) and 2-hydroxy-1-naphthaldehyde (0.172 g, 1 mmol) in 30 ml of ethanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Colourless crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a solution of the title compound in methanol.