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

Cui, J.; Li, C.; Qiao, Y.

doi:10.1107/S1600536812048088

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 (C-C) = 0.006 Å
R = 0.041
wR = 0.104
Data-to-parameter ratio = 13.6
Details

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

Jichun Cui,^a ^* Chuan Li ^a and Yanling Qiao ^a

^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-HN 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); Koketsu & Ishihara (2003); Geisler et al. (2004). For crystal structures of 1,3-selenazole derivatives, see: Shen et al. (2011); Shi & Zhao, (2007).

Experimental

Crystal data

C₁₀H₈ClNOSe
M_r = 272.58
Monoclinic, P 2₁ /c
a = 14.8150 (15) Å
b = 4.5707 (4) Å
c = 14.9123 (14) Å
= 96.642 (1)°
V = 1003.01 (16) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.337, T_max = 0.587
4466 measured reflections
1742 independent reflections
1318 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.104
S = 1.01
1742 reflections
128 parameters
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1ⁱ	0.82	2.07	2.891 (5)	174
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Koketsu, M. & Ishihara, H. (2003). Curr. Org. Chem. 7, 175-185.
Shafiee, A., Mazloumi, A. & Cohen, V. I. (1979). J. Heterocycl. Chem. 16, 1563-1566.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shen, J.-B., Lv, X., Chen, J.-F., Zhou, Y.-F. & Zhao, G.-L. (2011). Acta Cryst. E67, o803.
Shi, X. & Zhao, G.-L. (2007). Acta Cryst. E63, o3642.

organic compounds