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

Yan An; Xiaofeng Li; Yingjie Zhang

doi:10.1107/S1600536811045685

. 2011 Nov 12;67(Pt 12):o3278. doi: 10.1107/S1600536811045685

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

Yan An ^a, Xiaofeng Li ^a,^*, Yingjie Zhang ^a

PMCID: PMC3238935 PMID: 22199784

Abstract

In the title molecule, C₁₈H₁₃N₃O₄, the hydroxy group is involved in the formation of an intramolecular O—H⋯N hydrogen bond. The dihedral angle between the planes of the benzene ring and the naphthyl ring system is 9.0 (2)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds into chains along the c axis.

Related literature

For recently published crystal structures of hydrazone compounds, see: Horkaew et al. (2011 ▶); Fun et al. (2011 ▶); Su et al. (2011 ▶); Zhi et al. (2011 ▶).

Experimental

Crystal data

C₁₈H₁₃N₃O₄
M _r = 335.31
Monoclinic,
a = 11.208 (3) Å
b = 15.432 (3) Å
c = 8.982 (2) Å
β = 90.701 (2)°
V = 1553.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.980, T _max = 0.983
8323 measured reflections
2817 independent reflections
1564 reflections with I > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.127
S = 1.02
2817 reflections
232 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 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/S1600536811045685/cv5182sup1.cif

e-67-o3278-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045685/cv5182Isup2.hkl

e-67-o3278-Isup2.hkl^{(138.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811045685/cv5182Isup3.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	0.86 (1)	1.85 (2)	2.599 (3)	144 (3)
N2—H2⋯O2ⁱ	0.90 (1)	2.06 (1)	2.923 (3)	160 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the National Natural Science Foundation of China (21141007), Shanghai Natural Science Foundation (11ZR1414800), the ‘Chen Guang’ project supported by the Shanghai Municipal Education Commission and the Shanghai Education Development Foundation (09 C G52), the Project of Shanghai Municipal Education Commission (09YZ245, 10YZ111) and Shanghai Maritime University (20110017, 20110013) for financial support.

supplementary crystallographic information

Comment

As a continuation of structural studies of hydrazone compounds (Horkaew et al., 2011; Fun et al., 2011; Su et al., 2011; Zhi et al., 2011), we present here the title new hydrazone compound (I).

In (I) (Fig. 1), intramolecular O—H···N hydrogen bond (Table 1) and conjugation effects of the molecule lead to the flattening of the whole molecule. The dihedral angle between the benzene ring and the naphthyl ring is 9.0 (2)°. The bond lengths and angles are normal and comparable to those observed in the related structures (Horkaew et al., 2011; Fun et al., 2011; Su et al., 2011; Zhi et al., 2011).

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

Experimental

Equimolar quantities (0.5 mmol each) of 2-hydroxy-1-naphthaldehyde and 4-nitrobenzohydrazide were mixed in 30 ml me thanol. The mixture was stirred at reflux for 30 min and cooled to room temperature. Yellow block-shaped single crytals were formed by slow evaporation of the solvent in air.