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Volume 69 
Part 12 
Page o1838  
December 2013  

Received 31 October 2013
Accepted 15 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.001 Å
R = 0.039
wR = 0.087
Data-to-parameter ratio = 9.4
Details
Open access

2-[(Quinolin-8-yl­oxy)meth­yl]-1H-benzimid­a­zole monohydrate

aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, People's Republic of China
Correspondence e-mail: yonghwen@163.com

In the title hydrate, C17H13N3O·H2O, the dihedral angle between the quinoline and benzimidazole ring systems is 6.22 (7)°. The water mol­ecule is linked to the main mol­ecule by N-H...O and O-H...N hydrogen bonds. Further O-H...N hydrogen bonds link the organic molecules into C(6) chains running parallel to the b axis.

Related literature

For background to the properties and applications of benz­imidazole and 8-hy­droxy­quinoline and their derivatives, see: Hanna & Moawad (2002[Hanna, W. G. & Moawad, M. M. (2002). J. Coord. Chem. 55, 43-60.]); Patel & Patel (1999[Patel, A. K. & Patel, V. M. (1999). Synth. React. Inorg. Met.-Org. Chem. 29, 193-197.]); Pierre et al. (2003[Pierre, J.-L., Baret, P. & Serratrice, G. (2003). Curr. Med. Chem. 10, 1077-1084.]); Liu et al. (2005[Liu, Q.-D., Jia, W.-L. & Wang, S. (2005). Inorg. Chem. 44, 1332-1343.]); Wang et al. (2006[Wang, Y., Xu, H.-B., Su, Z.-M., Shao, K.-Z., Zhao, Y.-H., Cui, H.-P., Lan, Y.-Q. & Hao, X.-R. (2006). Inorg. Chem. Commun. 9, 1207-1211.]); Wen et al. (2011[Wen, Y.-H., Xie, X.-L. & Wang, L. (2011). J. Coord. Chem. 64, 459-472.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13N3O·H2O

  • Mr = 293.32

  • Orthorhombic, P 21 21 21

  • a = 6.1679 (12) Å

  • b = 11.094 (2) Å

  • c = 20.502 (4) Å

  • V = 1402.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.12 × 0.10 × 0.06 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.989, Tmax = 0.994

  • 10881 measured reflections

  • 1947 independent reflections

  • 1808 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.087

  • S = 1.06

  • 1947 reflections

  • 207 parameters

  • 18 restraints

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

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2WB...N1 0.87 (1) 2.03 (1) 2.8892 (10) 170 (1)
N2-H2A...O2 0.86 1.95 2.7880 (9) 163
O2-H2WA...N3i 0.86 (1) 2.05 (1) 2.9046 (9) 174 (1)
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2452 ).


Acknowledgements

This work was supported financially by the Science and Technology Project of Shandong Province, China (No. 2012 G0020221).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hanna, W. G. & Moawad, M. M. (2002). J. Coord. Chem. 55, 43-60.  [Web of Science] [CrossRef] [ChemPort]
Liu, Q.-D., Jia, W.-L. & Wang, S. (2005). Inorg. Chem. 44, 1332-1343.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Patel, A. K. & Patel, V. M. (1999). Synth. React. Inorg. Met.-Org. Chem. 29, 193-197.  [CrossRef] [ChemPort]
Pierre, J.-L., Baret, P. & Serratrice, G. (2003). Curr. Med. Chem. 10, 1077-1084.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wang, Y., Xu, H.-B., Su, Z.-M., Shao, K.-Z., Zhao, Y.-H., Cui, H.-P., Lan, Y.-Q. & Hao, X.-R. (2006). Inorg. Chem. Commun. 9, 1207-1211.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Wen, Y.-H., Xie, X.-L. & Wang, L. (2011). J. Coord. Chem. 64, 459-472.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1838  [ doi:10.1107/S1600536813031322 ]

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