3-(3-Methyl­phen­yl)-5-(quinolin-8-yl­meth­oxy)-1,2,4-oxa­diazole monohydrate

Lu Yang; Wei Liu; Han Wang; Xing-Wei Chen; Hai-Bo Wang

doi:10.1107/S160053681302477X

. 2013 Sep 12;69(Pt 10):o1541. doi: 10.1107/S160053681302477X

3-(3-Methylphenyl)-5-(quinolin-8-ylmethoxy)-1,2,4-oxadiazole monohydrate

Lu Yang ^a,^b, Wei Liu ^a,^b, Han Wang ^a,^b,^*, Xing-Wei Chen ^a,^b, Hai-Bo Wang ^b

PMCID: PMC3790408 PMID: 24098227

Abstract

In the title compound, C₁₉H₁₅N₃O₂·H₂O, the oxadiazole ring and the quinoline unit are almost coplanar, making a dihedral angle of 7.66 (8)°. The dihedral angle between the benzene ring and the quinoline system is 25.95 (8)° while that between the benzene and the oxadiazole rings is 18.88 (9)°. The water molecule is hydrogen bonded to an oxadiazole N atom and to the quinoline N atom. In the crystal, these units are linked via C—H⋯O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane.

Related literature

For the preparation of the title compound, see: Chiou & Shine (1989 ▶). For the biological activity of 1,2,4-oxadiazole derivatives, see: Street et al. (1990 ▶). For metal complexes of related compounds, see: da Silva et al. (1999 ▶); Pibiri et al. (2010 ▶); Terenzi et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₁₅N₃O₂·H₂O
M _r = 335.36
Triclinic,
a = 7.2070 (14) Å
b = 7.6200 (15) Å
c = 15.109 (3) Å
α = 92.62 (3)°
β = 90.19 (3)°
γ = 92.15 (3)°
V = 828.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.973, T _max = 0.991
3302 measured reflections
3039 independent reflections
1949 reflections with I > 2σ(I)
R _int = 0.015
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.162
S = 1.00
3039 reflections
233 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) D, I. DOI: 10.1107/S160053681302477X/im2428sup1.cif

e-69-o1541-sup1.cif^{(26.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302477X/im2428Isup2.hkl

e-69-o1541-Isup2.hkl^{(149.1KB, 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
OW—HWB⋯N2	0.91 (3)	2.09 (3)	2.980 (3)	169 (3)
OW—HWA⋯N1	0.94 (3)	1.91 (3)	2.830 (3)	165 (3)
C7—H7A⋯OW ⁱ	0.93	2.51	3.272 (3)	139
C10—H10A⋯OW ⁱⁱ	0.97	2.55	3.482 (3)	160
C10—H10B⋯OW ⁱⁱⁱ	0.97	2.59	3.534 (3)	164

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

supplementary crystallographic information

1. Comment

1,2,4-Oxadiazole derivatives have shown high biological activity, such as antibacterial, anti-HIV and weed control (Street et al., 1990). They are therefore widely used in medicinal chemistry and as pesticides. 1,2,4-Oxadiazole derivatives in combination with metal ions can also be used in fluorescent recognition (da Silva et al., 1999; Pibiri et al., 2010; Terenzi et al., 2011). The title compound 5-(quinoline-8-ylmethoxy)-3-p-tolyl-1,2,4-oxadiazole was also used in metal ions fluorescent recognition. In the molecule of 5-(quinoline-8-ylmethoxy)-3-p-tolyl-1,2,4-oxadiazole hydrate (Fig. 1) bond lengths (Allen et al., 1987) and angles are within normal ranges.The oxadiazol ring and the quinoline moiety are almost coplanar showing a dihedral angle of 7.66 (8)°. The dihedral angles between the benzene ring and the quinoline system is 25.95 (8)°, the corresponding angle between the benzene and the oxadiazol rings is 18.88 (9)°. The crystal structure is established by intermolecular N—H···O and O—H···O hydrogen bonds (Fig. 2).

2. Experimental

5-(Quinoline-8-ylmethoxy)-3-p-tolyl-1,2,4-oxadiazole was prepared by a literature method (Chiou & Shine, 1989). 3-(4-Methyl-phenyl)-5-chloromethyl-1,2,4-oxadizole (3.4 g, 16.4 mmol), 8-hydroxy-quinoline (2.4 g, 16.4 mmol), potassium carbonate (3.4 g ,24.6 mmol) and potassium iodide (catalytic amount) were added to acetone (40 ml). The mixture was then heated to reflux for 6 hours. After being cooled to room temperature, the mixture was filtered and evaporated to afford the product as a yellow solid. The crude product was re-crystallized from ethyl acetate (yield 3.1g, 59.8%). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.