(E)-N′-(3,4-Dimethoxy­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide–methanol–water (1/1/1)

Zhan-Ling Ma

doi:10.1107/S1600536809051034

. 2009 Nov 28;65(Pt 12):o3230. doi: 10.1107/S1600536809051034

(E)-N′-(3,4-Dimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide–methanol–water (1/1/1)

Zhan-Ling Ma ^a,^*

PMCID: PMC2972133 PMID: 21578936

Abstract

In the title compound, C₂₀H₁₉N₃O₄·CH₄O·H₂O, the Schiff base molecule is almost planar, with a dihedral angle of 1.2 (1)° between the benzene ring and the quinoline ring system. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, the methanol and water solvent molecules are linked to the Schiff base molecule via N—H⋯O, O—H⋯O, O—H⋯N and O—H⋯(O,N) hydrogen bonds.

Related literature

For background to the applications of 8-hydroxyquinoline and its derivatives, see: Bratzel et al. (1972 ▶); Karmakar et al. (2007 ▶); Pierre et al. (2003 ▶). For a Schiff base compound containing 2,5-dimethoxybenzaldehyde, see: Wang et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-65-o3230-scheme1.jpg

Experimental

Crystal data

C₂₀H₁₉N₃O₄·CH₄O·H₂O
M _r = 415.44
Triclinic,
a = 8.807 (2) Å
b = 10.071 (3) Å
c = 13.121 (3) Å
α = 68.702 (4)°
β = 74.552 (3)°
γ = 82.458 (5)°
V = 1044.4 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.21 × 0.18 × 0.16 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.980, T _max = 0.985
5612 measured reflections
3676 independent reflections
1571 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.126
S = 1.01
3676 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 global, I. DOI: 10.1107/S1600536809051034/hb5253sup1.cif

e-65-o3230-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051034/hb5253Isup2.hkl

e-65-o3230-Isup2.hkl^{(180.2KB, 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—H8⋯O1	0.86	2.35	2.698 (3)	105
N2—H8⋯O5ⁱ	0.86	2.06	2.899 (3)	165
O6—H6⋯O2	0.82	1.98	2.756 (4)	156
O6—H6⋯N3	0.82	2.58	3.194 (4)	133
O5—H21⋯N1ⁱⁱ	0.85	2.00	2.834 (4)	168
O5—H22⋯O6ⁱⁱⁱ	0.85	2.02	2.847 (4)	164

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

supplementary crystallographic information

Comment

8-Hydroxyquinoline and its derivatives have been used widely in analytical chemistry (Bratzel et al., 1972), coordination chemistry (Karmakar et al., 2007), pharmaceutical chemistry (Pierre et al., 2003) and many other topics. As part of our on going search for good extractants of metal ions or a biologically active material, the title compound was obtained in the reaction of quinolin-8-yloxyacetic acid hydrazide and 3,4-dimethoxybenzaldehyde.

The Schiff base molecule of the compound displays a trans configuration with respect to the C=N and C—N bonds(Fig. 1). All the bond lengths are within normal(Allen et al., 1987), and are comparable to those in the related compound (E)-N'-(2,5-Dimethoxybenzylidene)-2-(8- quinolyloxy)acetohydrazide methanol solvate (Wang et al., 2009). The molecule is nearly planar, with a dihedral angle of the benzene ring and the quinoline ring is 1.2 (1)°. The methanol and water solvate molecules are linked to the host via N—H···O, O—H···O and O—H···N hydrogen bonds(Table 1).

Experimental

3,4-Dimethoxybenzaldehyde (0.1 mmol, 16.6 mg) and 2-(quinolin-8-yloxy) acetohydrazide (2.18 g, 10 mmol), were dissolved in a 95% ethanol solution (10 ml). The mixture was stirred at room temperature to give a clear colorless solution. Colourless blocks of (I) were formed by gradual evaporation of the solvent over a period of six days at room temperature.