(E)-N′-(3,4,5-Trimethoxy­benzyl­idene)-2-(8-quinol­yloxy)acetohydrazide methanol solvate

Ling Zeng

doi:10.1107/S1600536809051113

. 2009 Dec 4;66(Pt 1):o23. doi: 10.1107/S1600536809051113

(E)-N′-(3,4,5-Trimethoxybenzylidene)-2-(8-quinolyloxy)acetohydrazide methanol solvate

Ling Zeng ^a,^*

PMCID: PMC2980132 PMID: 21580111

Abstract

In the title compound, C₂₁H₂₁N₃O₅·CH₄O, the quinoline plane and the benzene ring form a dihedral angle of 3.6 (2)°. The methanol solvent molecule is linked with the acetohydrazide molecule via O—H⋯N and N—H⋯O hydrogen bonds. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds help to consolidate the crystal packing, which also exhibits π–π interactions, as indicated by short distances of 3.739 (4) Å between the centroids of the aromatic rings.

Related literature

For applications of 8-hydroxyquinoline derivatives, see: Park et al. (2006 ▶); Karmakar et al. (2007 ▶). For a related structure, see Wang et al. (2009 ▶).

Experimental

Crystal data

C₂₁H₂₁N₃O₅·CH₄O
M _r = 427.45
Orthorhombic,
a = 13.385 (4) Å
b = 4.9005 (15) Å
c = 31.89 (1) Å
V = 2091.8 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.18 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.982, T _max = 0.988
10056 measured reflections
1879 independent reflections
1263 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.099
S = 1.08
1879 reflections
283 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 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/S1600536809051113/cv2668sup1.cif

e-66-00o23-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051113/cv2668Isup2.hkl

e-66-00o23-Isup2.hkl^{(92.5KB, 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
O6—H6⋯N1	0.82	2.02	2.814 (5)	164
N2—H4⋯O6	0.86	2.30	3.070 (4)	149
C3—H3⋯O5ⁱ	0.93	2.45	3.340 (6)	159
C5—H5⋯O4ⁱ	0.93	2.52	3.411 (6)	160
C19—H19A⋯O2ⁱⁱ	0.96	2.37	3.196 (6)	144
C21—H21A⋯O3ⁱⁱⁱ	0.96	2.57	3.265 (5)	130

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

supplementary crystallographic information

Comment

Synthesis of 8-hydroxyquinoline and its derivatives have attracted a great interest due to their biological activities and applications in coordination chemistry (Park et al., 2006; Karmakar et al., 2007). In our search for new extractants of metal ions and biologically active materials, the title compound, (I), has been synthesized. We report here its crystal structure.

All bond lengths and angles are normal and comparable to those observed 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 of 3.6 (2)°. The methanol solvent molecule forms an O—H···N hydrogen bond to the quinoline ring system and accepts an N—H···O hydrogen bond from the hydrazide NH group. In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) help to consolidate the crystal packing.

Experimental

3,4,5-Trimethoxybenzaldehyde (0.1 mmol, 19.6 mg) and 2-(quinolin-8-yloxy) acetohydrazide (21.8 mg, 0.1 mmol), were dissolved in methanol (20 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of six days at room temperature.