(S)-tert-Butyl 3-(3-phenyl-1,2,4-oxa­diazol-5-yl)piperidine-1-carboxyl­ate

Liu, L.; Xia, G.; Liu, X.; Xie, J.; Shen, J.

doi:10.1107/S1600536810018714

Volume 66
Part 7
Page o1576
July 2010

Received 19 April 2010
Accepted 19 May 2010
Online 5 June 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.008 Å
R = 0.073
wR = 0.198
Data-to-parameter ratio = 7.4
Details

(S)-tert-Butyl 3-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate

Lin Liu,^a Guangxin Xia,^b Xuejun Liu,^b Jieshu Xie ^b and Jingkang Shen ^a ^*

^aShanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, People's Republic of China, and ^bCentral Research Institute, Shanghai Pharmaceutical (Group) Co. Ltd, 555 Zuchongzhi Road, Shanghai 201203, People's Republic of China
Correspondence e-mail: jkshen@mail.shcnc.ac.cn

The title compound, C₁₈H₂₃N₃O₃, crystallized with two independent molecules (A and B) in the asymmetric unit. The phenyl ring and the 1,2,4-oxadiazole ring are inclined to one another by 19.9 (3)° in molecule A and 7.3 (3)° in molecule B. The absolute structure of the title compound was referred to the transfered chiral center (S) of one of the starting reactants. In the crystal, A molecules are linked by C-HN interactions involving the two oxadiazole N atoms.

Related literature

For the oxadiazole nucleus as a core structural unit of various muscarinic agonists, see: Orlek & Blaney (1991). For benzodiazepine receptor partial agonists, see: Watjen & Baker (1989). For dopamine transporters, see: Gray & Abrahm (1993). For 5-HT agonists, see: Swain & Baker (1991). For inhibitors of HIV, see: Matthew et al. (2007). For GABAA receptor agonists, see: Michaela & Holger (2008). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₈H₂₃N₃O₃
M_r = 329.39
Monoclinic, P 2₁
a = 6.464 (3) Å
b = 15.515 (8) Å
c = 17.847 (9) Å
= 99.880 (7)°
V = 1763.2 (15) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.24 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008) T_min = 0.980, T_max = 0.990
7378 measured reflections
3258 independent reflections
2520 reflections with I > 2(I)
R_int = 0.073

Refinement

R[F² > 2(F²)] = 0.073
wR(F²) = 0.198
S = 1.01
3258 reflections
440 parameters
1 restraint
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C13-H13AN2ⁱ	0.97	2.61	3.352 (7)	133
C18-H18AN1ⁱ	0.96	2.61	3.490 (9)	153
Symmetry code: (i) x+1, y, z.

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2175 ).

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.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gray, L. & Abrahm, P. (1993). J. Med. Chem. 36, 2886-2890.
Matthew, D. C., Deng, B.-L., Hartmann, T. L., Watson, K. M., Buckheit, R. W. Jr, Pannecouque, C., De Clercq, E. & Cushman, M. (2007). J. Med. Chem. 50, 4854-4867.
Michaela, J. & Holger, R. (2008). J. Med. Chem. 51, 4430-4448.
Orlek, B. S. & Blaney, F. E. (1991). J. Med. Chem. 34, 2726-2735.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Swain, C. & Baker, R. (1991). J. Med. Chem. 34, 140-151.
Watjen, F. & Baker, R. (1989). J. Med. Chem. 32, 2282-2291.

organic compounds