{4-[5-(4-tert-Butyl­phen­yl)-1,3,4-oxa­diazol-2-yl]phen­yl}methanol

Zhao, Y.-L.; Lv, Z.; Tian, B.; Hou, Z.; Geng, Z.-R.

doi:10.1107/S1600536810052967

Volume 67
Part 2
Page o251
February 2011

Received 2 December 2010
Accepted 16 December 2010
Online 8 January 2011

Key indicators
Single-crystal X-ray study
T = 185 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.122
Data-to-parameter ratio = 13.6
Details

{4-[5-(4-tert-Butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}methanol

Yu-Ling Zhao,^a ^* Zhe Lv,^a Bin Tian,^a Zhe Hou ^a and Zhong-Rong Geng ^b

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China, and ^bKey Laboratory of Opto-Electronic Technology and Intelligent Control, Ministry of Education, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
Correspondence e-mail: zhaoyl66@hotmail.com

In the title compound, C₁₉H₂₀N₂O₂, the 1,3,4-oxadiazole ring is almost coplanar with the two neighboring benzene rings [dihedral angles = 3.76 (4) and 5.49 (4)°]. In the crystal, molecules are connected by strong intermolecular O-HN hydrogen bonds, forming chains parallel to the c axis.

Related literature

For the properties and applications of 1,3,4-oxadiazole derivatives, see: Hughes & Bryce (2005); Kim & Lee (2007); Kulkarni et al. (2004); Liang et al. (2003); Liou et al. (2006); Strukelj et al. (1995). For the biological activity of compounds containing the 1,3,4-oxadiazole moiety, see: Cacic et al. (2006); Mansour et al. (2003); Yar et al. (2007); Zhang et al. (2007). For synthesis of the intermediate, see Mashraqui et al. (2007).

Experimental

Crystal data

C₁₉H₂₀N₂O₂
M_r = 308.37
Monoclinic, P 2₁ /c
a = 16.3958 (18) Å
b = 6.0654 (7) Å
c = 16.7206 (19) Å
= 102.289 (2)°
V = 1624.7 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 185 K
0.32 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.974, T_max = 0.993
8995 measured reflections
2886 independent reflections
1805 reflections with I > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.122
S = 0.98
2886 reflections
212 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N2ⁱ	0.84	2.07	2.906 (3)	179
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: PK2290 ).

Acknowledgements

This work was supported by the Natural Science Foundation of Gansu Province (096RJZA086) and the project of students' science and technology innovation funds (DXS2010-041) of Lanzhou Jiaotong University.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cacic, M., Trkovnik, M., Cacic, F. & Has-Schon, E. (2006). Molecules, 11, 134-147.
Hughes, G. & Bryce, M. R. (2005). J. Mater. Chem. 15, 94-107.
Kim, J. H. & Lee, H. (2007). Synth. Met. 157, 1040-1045.
Kulkarni, A. P., Tonzola, C. J., Babel, A. & Jenekhe, S. A. (2004). Chem. Mater. 16, 4556-4573.
Liang, F. S., Zhou, Q. G., Cheng, Y. X., Wang, L. X., Ma, D. G., Jing, X. B. & Wang, F. S. (2003). Chem. Mater. 15, 1935-1937.
Liou, G. S., Hsiao, S. H., Chen, W. C. & Yen, H. J. (2006). Macromolecules, 39, 6036-6045.
Mansour, A. K., Eid, M. M. & Khalil, N. S. A. M. (2003). Molecules, 8, 744-755.
Mashraqui, S. H., Sundaram, S., Bhasikuttan, A. C., Kapoor, S. & Sapre, A. V. (2007). Senss. Actuat. B, 122, 347-350.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Strukelj, M., Papadimitrakopoulos, F., Miller, T. M. & Rothberg, L. J. (1995). Science, 267, 1969-1972.
Yar, M. S., Siddiqui, A. A. & Ali, M. A. (2007). J. Chin. Chem. Soc. 54, 5-8.
Zhang, C. R., Wang, L., Ge, Y. L. & Ju, X. L. (2007). Chin. J. Org. Chem. 27, 1432-1437.

organic compounds