(E)-N′-(3,4-Dimethoxy­benzyl­idene)-2,4-dihydroxy­benzohydrazide methanol solvate

Qiao-Ling Zhang; Li-Zi Yin; Xu-Ming Deng; Song-Cai Liu; De-Guang Song

doi:10.1107/S1600536809035752

. 2009 Sep 9;65(Pt 10):o2392–o2393. doi: 10.1107/S1600536809035752

(E)-N′-(3,4-Dimethoxybenzylidene)-2,4-dihydroxybenzohydrazide methanol solvate

Qiao-Ling Zhang ^a, Li-Zi Yin ^a, Xu-Ming Deng ^a, Song-Cai Liu ^a,^*, De-Guang Song ^a,^*

PMCID: PMC2970482 PMID: 21577856

Abstract

The title compound, C₁₆H₁₆N₂O₅·CH₃OH, was obtained from a condensation reaction of 3,4-dimethoxybenzaldehyde and 2,4-dihydroxybenzohydrazide. The non-H atoms of the Schiff base molecule are approximately coplanar (r.m.s. deviation = 0.043 Å) and the dihedral angle between the two benzene rings is 1.6 (1)°. The molecule adopts an E configuration with respect to the C=N double bond. An intramolecular O—H⋯O hydrogen bond is observed. The Schiff base and methanol molecules are linked into a two-dimensional network parallel to (10 Inline graphic ) by intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For background to Schiff base compounds, hydrazone compounds and their biological properties, see: Kucukguzel et al. (2006 ▶); Khattab et al. (2005 ▶); Karthikeyan et al. (2006 ▶); Okabe et al. (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Shan et al. (2008 ▶); Fun et al. (2008 ▶); Ma et al. (2008 ▶); Diao et al. (2008a ▶,b ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₅·CH₄O
M _r = 348.35
Monoclinic,
a = 8.497 (1) Å
b = 17.431 (2) Å
c = 11.933 (2) Å
β = 102.93 (2)°
V = 1722.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.25 × 0.23 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.975, T _max = 0.977
10465 measured reflections
3732 independent reflections
2017 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.129
S = 1.03
3732 reflections
235 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.19 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/S1600536809035752/ci2900sup1.cif

e-65-o2392-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035752/ci2900Isup2.hkl

e-65-o2392-Isup2.hkl^{(183KB, 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
N1—H1A⋯O2ⁱ	0.90 (1)	2.217 (10)	3.108 (2)	170 (2)
O6—H6⋯N2ⁱⁱ	0.82	2.55	3.133 (2)	129
O6—H6⋯O3ⁱⁱ	0.82	2.02	2.807 (2)	161
O2—H2⋯O6ⁱⁱⁱ	0.82	1.79	2.599 (2)	171
O1—H1⋯O3	0.82	1.80	2.534 (2)	148

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

supplementary crystallographic information

Comment

Hydrazones and Schiff bases have been attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab et al., 2005; Karthikeyan et al., 2006; Okabe et al., 1993). Recently, a large number of hydrazone derivatives have been prepared and structurally characterized (Shan et al., 2008; Fun et al., 2008; Ma et al., 2008; Diao et al., 2008a,b; Ejsmont et al., 2008). As part of the ongoing study, we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The compound consists of a Schiff base molecule and a methanol molecule. The dihedral angle between the two benzene rings is 1.6 (1)°. The Schiff base molecule displays an E configuration about the C═N bond. The bond lengths are typical (Allen et al., 1987). The molecules are linked into a two-dimensional network parallel to the (101) by intermolecular N—H···O, O—H···N, and O—H···O hydrogen bonds (Fig. 2 and Table 1).

Experimental

3,4-Dimethoxybenzaldehyde (1.0 mmol, 166.2 mg) was dissolved in methanol (50 ml), then 2,4-dihydroxybenzohydrazide (1.0 mmol, 168.2 mg) was added slowly into the solution, and the mixture was kept at reflux with continuous stirring for 1 h. After the solution had cooled to room temperature colourless crystallites appeared. The crystallites were filtered and washed with methanol for three times. Recrystallization from an absolute methanol yielded block-shaped single crystals of the title compound.