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Volume 68 
Part 12 
Page o3458  
December 2012  

Received 2 November 2012
Accepted 22 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.006 Å
R = 0.041
wR = 0.104
Data-to-parameter ratio = 13.6
Details
Open access

[2-(4-Chlorophenyl)-1,3-selenazol-4-yl]methanol

aShandong Provincial Key Laboratory of Chemical Energy Storage, and Novel Cell Technology, School of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
Correspondence e-mail: jchcui@163.com

In the title compound, C10H8ClNOSe, the dihedral angle between benzene and selenazole rings is 11.4 (3)° and the hydroxymethyl group is bent from the selenazole ring, making a dihedral angle of 63.8 (3)°. In the crystal, molecules are linked into inversion dimers by pairs of O-H...N hydrogen bonds. Roof-tile-like stacking of the molecules along [010] [b = 4.5707 (4) Å] is observed, with the benzene and selenazole rings separated by a face-to-face distance of 3.57 Å and a mutual slippage of 2.85 Å.

Related literature

For the synthesis of 1,3-selenazoles and their biological activity, see: Shafiee et al. (1979[Shafiee, A., Mazloumi, A. & Cohen, V. I. (1979). J. Heterocycl. Chem. 16, 1563-1566.]); Koketsu & Ishihara (2003[Koketsu, M. & Ishihara, H. (2003). Curr. Org. Chem. 7, 175-185.]); Geisler et al. (2004[Geisler, K., Künzler, A., Below, H., Bulka, E., Pfeiffer, W.-D. & Langer, P. (2004). Synthesis, pp. 97-105.]). For crystal structures of 1,3-selenazole derivatives, see: Shen et al. (2011[Shen, J.-B., Lv, X., Chen, J.-F., Zhou, Y.-F. & Zhao, G.-L. (2011). Acta Cryst. E67, o803.]); Shi & Zhao, (2007[Shi, X. & Zhao, G.-L. (2007). Acta Cryst. E63, o3642.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8ClNOSe

  • Mr = 272.58

  • Monoclinic, P 21 /c

  • a = 14.8150 (15) Å

  • b = 4.5707 (4) Å

  • c = 14.9123 (14) Å

  • [beta] = 96.642 (1)°

  • V = 1003.01 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.97 mm-1

  • T = 298 K

  • 0.35 × 0.32 × 0.15 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.337, Tmax = 0.587

  • 4466 measured reflections

  • 1742 independent reflections

  • 1318 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.104

  • S = 1.01

  • 1742 reflections

  • 128 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.82 2.07 2.891 (5) 174
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2047 ).


Acknowledgements

We acknowledge the National Natural Foundation of China (21105042), the National Basic Research Program (2010CB234601) and the Natural Science Foundation of Shandong Province (ZR2011BM007, ZR2010BQ021) for financial support.

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Geisler, K., Künzler, A., Below, H., Bulka, E., Pfeiffer, W.-D. & Langer, P. (2004). Synthesis, pp. 97-105.  [CrossRef]
Koketsu, M. & Ishihara, H. (2003). Curr. Org. Chem. 7, 175-185.  [ISI] [CrossRef] [ChemPort]
Shafiee, A., Mazloumi, A. & Cohen, V. I. (1979). J. Heterocycl. Chem. 16, 1563-1566.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shen, J.-B., Lv, X., Chen, J.-F., Zhou, Y.-F. & Zhao, G.-L. (2011). Acta Cryst. E67, o803.  [CSD] [CrossRef] [details]
Shi, X. & Zhao, G.-L. (2007). Acta Cryst. E63, o3642.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3458  [ doi:10.1107/S1600536812048088 ]

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