2,4-Dihydr­oxy-N′-(4-methoxy­benzyl­idene)benzohydrazide

Yun-Peng Diao; Shan-Shan Huang; Jian-Kui Zhang; Ting-Guo Kang

doi:10.1107/S1600536808001104

. 2008 Jan 18;64(Pt 2):o470. doi: 10.1107/S1600536808001104

2,4-Dihydroxy-N′-(4-methoxybenzylidene)benzohydrazide

Yun-Peng Diao ^a, Shan-Shan Huang ^a, Jian-Kui Zhang ^b, Ting-Guo Kang ^b,^*

PMCID: PMC2960241 PMID: 21201496

Abstract

The molecule of the title compound, C₁₅H₁₄N₂O₄, displays a trans configuration with respect to the hydrazide C=N bond. The dihedral angle between the two benzene rings is 15.0 (2)°. In the crystal structure, molecules are linked through intermolecular O—H⋯N and O—H⋯O hydrogen bonds, forming layers parallel to the ab plane; an intramolecular N—H⋯O hydrogen bond is also present.

Related literature

For the biological properties of Schiff base compounds, see: Brückner et al. (2000 ▶); Harrop et al. (2003 ▶); Ren et al. (2002 ▶). For related structures, see: Diao (2007 ▶); Diao et al. (2007 ▶); Li et al. (2007 ▶); Huang et al. (2007 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O₄
M _r = 286.28
Orthorhombic,
a = 12.494 (3) Å
b = 5.196 (1) Å
c = 20.825 (4) Å
V = 1351.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.978, T _max = 0.980
7661 measured reflections
1519 independent reflections
1382 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.079
S = 1.06
1519 reflections
196 parameters
2 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, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536808001104/rz2192sup1.cif

e-64-0o470-sup1.cif^{(15.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001104/rz2192Isup2.hkl

e-64-0o470-Isup2.hkl^{(74.9KB, 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—H2A⋯O3	0.901 (10)	1.94 (2)	2.646 (2)	134 (3)
O4—H4⋯O2ⁱ	0.82	1.85	2.671 (2)	174
O3—H3⋯N1ⁱⁱ	0.82	2.48	3.234 (2)	154
O3—H3⋯O2ⁱⁱ	0.82	2.14	2.788 (2)	136

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

Acknowledgments

This project was supported by a research grant from Dalian Medical University.

supplementary crystallographic information

Comment

Schiff base compounds have received much attention in recent years. Some Schiff base metal complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on the synthesis and characterization of Schiff base compounds (Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title ligand.

The molecule of the title compound displays a trans configuration with respect to the C=N bond (Fig. 1). The dihedral angle between the two benzene rings is 15.0 (2)°. The molecular conformation is stabilized by an intramolecular N—H···O hydrogen interaction (Table 1). In the crystal, molecules are linked through intermolecular O—H···N and O—H···O hydrogen bonds (Table 1), forming layers parallel to the ab plane (Fig. 2).

Experimental

4-Methoxybenzaldehyde (0.1 mmol, 13.6 mg) and 2,4-dihydroxybenzoic acid hydrazide (0.1 mmol, 16.8 mg) were dissolved in a 95% ethanol solution (10 ml). The mixture was stirred at room temperature to give a clear colourless solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of three days at room temperature.