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Volume 69 
Part 5 
Page o760  
May 2013  

Received 18 March 2013
Accepted 15 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.055
wR = 0.195
Data-to-parameter ratio = 12.7
Details
Open access

8-{[3-(3-Methoxyphenyl)-1,2,4-oxadiazol-5-yl]methoxy}quinoline monohydrate

aCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and bCollege of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: wanghaibo@njut.edu.cn

In the title hydrate, C19H15N3O3·H2O, the three aromatic groups in the quinoline derivative are close to coplanar: the central oxadiazole fragment makes dihedral angles of 15.7 (2)° with the benzene ring and 5.30 (14)° with the quinoline ring system. In the crystal, the organic molecules are connected with water molecules by pairs of O-H...N hydrogen bonds involving the quinoline and oxadiazole N atoms. The molecules form stacks along the a axis, neighboring molecules within each stack being related by inversion and the shortest distance between the centroids of the oxadiazole and pyridine rings being 3.500 (2) Å. Molecules from neighboring stacks are linked by weak C-H...O hydrogen bonds, forming a three-dimensional structure.

Related literature

For the preparation of the title compound, see: Shishue & Henry (1989[Shishue, C. & Henry, J. S. (1989). J. Heterocycl. Chem., 26, 125-128.]). For the general synthetic procedure, see: Munoz-Muniz & Juaristi (2003[Munoz-Muniz, O. & Juaristi, E. (2003). Tetrahedron, 59, 4223-4229.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15N3O3·H2O

  • Mr = 351.36

  • Monoclinic, P 21 /n

  • a = 7.9510 (16) Å

  • b = 6.9870 (14) Å

  • c = 30.395 (6) Å

  • [beta] = 92.31 (3)°

  • V = 1687.2 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.971, Tmax = 0.990

  • 3339 measured reflections

  • 3101 independent reflections

  • 2183 reflections with I > 2[sigma](I)

  • Rint = 0.056

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.195

  • S = 1.01

  • 3101 reflections

  • 244 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
OW-HWB...N2 0.92 (5) 2.05 (5) 2.965 (3) 174 (5)
OW-HWA...N3 0.88 (4) 1.96 (4) 2.840 (4) 172 (4)
C10-H10A...OWi 0.97 2.39 3.340 (4) 165
C16-H16A...O1ii 0.93 2.58 3.309 (4) 135
Symmetry codes: (i) x, y-1, z; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft. The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2090 ).


References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft. The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Munoz-Muniz, O. & Juaristi, E. (2003). Tetrahedron, 59, 4223-4229.  [ChemPort]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shishue, C. & Henry, J. S. (1989). J. Heterocycl. Chem., 26, 125-128.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o760  [ doi:10.1107/S1600536813010271 ]

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