(E)-N′-(2-Hydroxy­benzyl­idene)-3,4,5-trimethoxy­benzohydrazide

Yu-Min Wang; Zhen-Dong Zhao; Yu-Xiang Chen; Liang-Wu Bi

doi:10.1107/S1600536808006077

. 2008 May 7;64(Pt 6):o1009. doi: 10.1107/S1600536808006077

(E)-N′-(2-Hydroxybenzylidene)-3,4,5-trimethoxybenzohydrazide

Yu-Min Wang ^a, Zhen-Dong Zhao ^a,^*, Yu-Xiang Chen ^a, Liang-Wu Bi ^a

PMCID: PMC2961635 PMID: 21202535

Abstract

The title compound, C₁₇H₁₈N₂O₅, was synthesized from 3,4,5-trimethoxybenzohydrazide and 2-hydroxybenzaldehyde. The dihedral angle between the planes of the two benzene rings is 29.9 (2)°. The crystal structure involves intramolecular O—H⋯N, and intermolecular N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related literature, see: Yang et al. (1996 ▶); Nawar et al. (2000 ▶). Gardner et al. (1991 ▶); Labouta et al. (1989 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₅
M _r = 330.33
Monoclinic,
a = 15.348 (12) Å
b = 13.330 (11) Å
c = 8.299 (7) Å
β = 99.854 (16)°
V = 1673 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 (2) K
0.10 × 0.06 × 0.04 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.991, T _max = 0.995
8200 measured reflections
2952 independent reflections
1945 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.194
S = 1.00
2952 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536808006077/at2541sup1.cif

e-64-o1009-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006077/at2541Isup2.hkl

e-64-o1009-Isup2.hkl^{(144.9KB, 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
O1—H1⋯N1	0.82	1.94	2.670 (4)	147
N2—H2⋯O2ⁱ	0.86	2.00	2.826 (4)	161 (1)
C7—H7⋯O2ⁱ	0.93	2.48	3.240 (5)	139

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Natural Science Fund of Jiangsu Province (No. BK2006012).

supplementary crystallographic information

Comment

3,4,5-Trimethoxybenzohydrazide and their deviatives show moderate fungicidal and anti-bacterial activities (Gardner et al.,1991). The antibacterial activity of formylhydrazines and formylhydrazones has been reported by Labouta et al. (1989). Many derivatives of formylhydrazines have interesting biological properties. So we synthesized the title compound (I) and report here its crystal structure.

The molecular structure of (I) is shown in Fig. 1, where the dash lines indicate N–H···O and O—H···N hydrogen bonds (Table 2). The atoms C7, N1, N2, C8 and O2 almost share a same plane for its delocalized structure. The dihedral angle between the planes of the two phenyl rings is 29.9 (217)°.

In the crystal structure, there is a intramolecular O—H···N hydrogen bond and two intermolecular N—H···O and C—H···O hydrogen bonds.

Experimental

An ethanol solution (50 ml) of 3,4,5-trimethoxybenzohydrazide (0.01 mol) and 2-hydroxybenzaldehyde (0.01 mol) was refluxed and stirred for 4 h. The mixture was cooled and the resulting solid product, (I), was collected by filtration. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in THF.