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Volume 69 
Part 7 
Page o1034  
July 2013  

Received 17 May 2013
Accepted 27 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.052
wR = 0.144
Data-to-parameter ratio = 12.8
Details
Open access

8-[(3-Phenyl-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 compound, C18H13N3O2·H2O, the oxadiazole ring forms dihedral angles 7.21 (10) and 21.25 (11)° with the quinoline and benzene rings, respectively. The crystal structure features O-H...N hydrogen bonds and is further consolidated by C-H...O hydrogen-bonding interactions involving the water molecule of hydration.

Related literature

For general background, see: Katritzky et al. (1992[Katritzky, A. R., Ji, F. B. & Fan, W. Q. (1992). Heterocycl. Chem. 29, 1519-1523.]). For preparation of the title compound, see: Shishue & Henry (1989[Shishue, C. & Henry, J. S. (1989). J Heterocycl. Chem. 26, 125-128.]). For crystal structure of a related compound, see: Liu et al. (2006[Liu, Z.-Q., Wang, H.-B., Pu, Y.-Q. & Yan, X.-C. (2006). Acta Cryst. E62, o1131-o1132.]).

[Scheme 1]

Experimental

Crystal data
  • C18H13N3O2·H2O

  • Mr = 321.33

  • Monoclinic, P 21 /n

  • a = 7.0430 (14) Å

  • b = 7.5800 (15) Å

  • c = 29.114 (6) Å

  • [beta] = 95.33 (3)°

  • V = 1547.6 (5) 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 = 0.972, Tmax = 0.990

  • 3101 measured reflections

  • 2853 independent reflections

  • 1608 reflections with I > 2[sigma](I)

  • Rint = 0.025

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.144

  • S = 0.95

  • 2853 reflections

  • 223 parameters

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

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1W...N2 0.79 (4) 2.20 (4) 2.988 (3) 171 (4)
O1W-H2W...N3 0.81 (4) 2.00 (4) 2.810 (3) 174 (4)
C9-H9A...O1Wi 0.97 2.54 3.437 (3) 154
C12-H12A...O1Wii 0.93 2.51 3.268 (4) 139
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y+2, -z+1.

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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2633 ).


References

Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Katritzky, A. R., Ji, F. B. & Fan, W. Q. (1992). Heterocycl. Chem. 29, 1519-1523.  [CrossRef] [ChemPort]
Liu, Z.-Q., Wang, H.-B., Pu, Y.-Q. & Yan, X.-C. (2006). Acta Cryst. E62, o1131-o1132.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shishue, C. & Henry, J. S. (1989). J Heterocycl. Chem. 26, 125-128.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1034  [ doi:10.1107/S1600536813014529 ]

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