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Volume 69 
Part 10 
Page o1541  
October 2013  

Received 3 April 2013
Accepted 5 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.162
Data-to-parameter ratio = 13.0
Details
Open access

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

aCollege of Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China, and bCollege of Food Science and Light Industry, 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, 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[Chiou, S. & Shine, H. J. (1989). J. Heterocycl. Chem. 26, 125-128.]). For the biological activity of 1,2,4-oxadiazole derivatives, see: Street et al. (1990[Street, L. J., Baker, R., Book, T., Kneen, C. O., MacLeod, A. M., Merchant, K. J., Showell, G. A., Saunders, J., Herbert, R. H., Freedman, S. B. & Harley, E. A. (1990). J. Med. Chem. 33, 2690-2697.]). For metal complexes of related compounds, see: da Silva et al. (1999[Silva, A. S. da, de Silva, M. A. A., Carvalho, C. E. M., Antunes, O. A. C., Herrera, J. O. M., Brinn, I. M. & Mangrich, A. S. (1999). Inorg. Chim. Acta 292, 1-6.]); Pibiri et al. (2010[Pibiri, I., Piccionello, A. P., Calabrese, A., Buscemi, S., Vivona, N. & Pace, A. (2010). Eur. J. Org. Chem. pp. 4549-4553.]); Terenzi et al. (2011[Terenzi, A., Barone, G., Piccionello, A. P., Giorgi, G., Guarecello, A. & Pace, A. (2011). Inorg. Chim. Acta, 373, 62-67.]). For 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
  • C19H15N3O2·H2O

  • Mr = 335.36

  • Triclinic, [P \overline 1]

  • a = 7.2070 (14) Å

  • b = 7.6200 (15) Å

  • c = 15.109 (3) Å

  • [alpha] = 92.62 (3)°

  • [beta] = 90.19 (3)°

  • [gamma] = 92.15 (3)°

  • V = 828.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.10 × 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 = 0.973, Tmax = 0.991

  • 3302 measured reflections

  • 3039 independent reflections

  • 1949 reflections with I > 2[sigma](I)

  • Rint = 0.015

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.162

  • S = 1.00

  • 3039 reflections

  • 233 parameters

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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
OW-HWB...N2 0.91 (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...OWi 0.93 2.51 3.272 (3) 139
C10-H10A...OWii 0.97 2.55 3.482 (3) 160
C10-H10B...OWiii 0.97 2.59 3.534 (3) 164
Symmetry codes: (i) -x-1, -y+1, -z+2; (ii) x+1, y, z; (iii) -x, -y+2, -z+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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2428 ).


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.
Chiou, S. & Shine, H. J. (1989). J. Heterocycl. Chem. 26, 125-128.  [CrossRef] [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Pibiri, I., Piccionello, A. P., Calabrese, A., Buscemi, S., Vivona, N. & Pace, A. (2010). Eur. J. Org. Chem. pp. 4549-4553.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Silva, A. S. da, de Silva, M. A. A., Carvalho, C. E. M., Antunes, O. A. C., Herrera, J. O. M., Brinn, I. M. & Mangrich, A. S. (1999). Inorg. Chim. Acta 292, 1-6.
Street, L. J., Baker, R., Book, T., Kneen, C. O., MacLeod, A. M., Merchant, K. J., Showell, G. A., Saunders, J., Herbert, R. H., Freedman, S. B. & Harley, E. A. (1990). J. Med. Chem. 33, 2690-2697.
Terenzi, A., Barone, G., Piccionello, A. P., Giorgi, G., Guarecello, A. & Pace, A. (2011). Inorg. Chim. Acta, 373, 62-67.  [Web of Science] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1541  [ doi:10.1107/S160053681302477X ]

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