4-{(E)-N′-[2-(8-Quinolyloxy)acetyl]hydrazonomethyl}benzoic acid methanol solvate

Chun-Yan Ren

doi:10.1107/S1600536809021576

. 2009 Jun 17;65(Pt 7):o1601. doi: 10.1107/S1600536809021576

4-{(E)-N′-[2-(8-Quinolyloxy)acetyl]hydrazonomethyl}benzoic acid methanol solvate

Chun-Yan Ren ^a,^*

PMCID: PMC2969234 PMID: 21582875

Abstract

In the title compound, C₁₉H₁₅N₃O₄·CH₄O, the mean planes of the benzene ring and the quinoline system make a dihedral angle of 6.7 (2)°. The acetohydrazide host molecules are connected via intermolecular O—H⋯O hydrogen bonds into two-dimensional zigzag sheets extending in the ab plane. The methanol solvent molecule is linked to the host molecule via intermolecular N—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the coordination chemistry of 8-hydroxyquinoline and its derivatives, see: Chen & Shi (1998 ▶). For a related structure, see: Wen et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₁₅N₃O₄·CH₄O
M _r = 381.38
Monoclinic,
a = 10.1166 (18) Å
b = 11.095 (2) Å
c = 18.510 (3) Å
β = 115.896 (7)°
V = 1869.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.22 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.979, T _max = 0.982
9663 measured reflections
3302 independent reflections
1666 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.161
S = 1.02
3302 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 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/S1600536809021576/cs2119sup1.cif

e-65-o1601-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021576/cs2119Isup2.hkl

e-65-o1601-Isup2.hkl^{(162KB, 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
O3—H3⋯O2ⁱ	0.82	1.88	2.695 (3)	171
O5—H5⋯N1	0.82	1.95	2.765 (3)	171
N2—H2⋯O5	0.86	2.01	2.838 (4)	162

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

8-Hydroxyquinoline and its derivatives constitute well known ligands in coordination chemistry (Chen & Shi, 1998). 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 4-formylbenzoic acid. In the crystal structure of all bond lengths and angles are normal (Allen et al., 1987), and are comparable to those in the related compound N'-(2-Fluorobenzylidene)-2-(quinolin-8-yloxy)-acetohydrazide methanol solvate (Wen et al., 2005). The mean planes of the benzene ring and the quinoline ring make a dihedral angle of 6.7 (2)°. In the crystal structure, the methanol molecule is linked to the C₁₉H₁₅N₃O₄ host molecule via intermolecular N—H···O and O—H···N hydrogen bonds (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) fuse the molecules into two-dimensional zig-zag sheets along the a*-b* plane (Fig. 2).

Experimental

2-(quinolin-8-yloxy)acetohydrazide (2.18 g, 10 mmol), 4-formylbenzoic acid (1.50 g, 10 mmol), ethanol (40 ml) and some drops of acetic acid were added to a 100 ml flask, and refluxed for 3 h. After cooling to room temperature, the mixture was filtered. Colourless single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a acetone-methanol (1:2, v/v) solution over a period of 2 d.