3-Bromo-5-meth­oxy-4-(4-methyl­piperidin-1-yl)furan-2(5H)-one

Wei, X.-P.; Fu, J.-H.; Tan, Y.-H.; Wang, Z.-Y.

doi:10.1107/S1600536811008804

Volume 67
Part 4
Page o862
April 2011

Received 22 January 2011
Accepted 8 March 2011
Online 12 March 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
R = 0.049
wR = 0.109
Data-to-parameter ratio = 15.4
Details

3-Bromo-5-methoxy-4-(4-methylpiperidin-1-yl)furan-2(5H)-one

Xin-Ping Wei,^a Jian-Hua Fu,^a Yue-He Tan ^a and Zhao-Yang Wang ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
Correspondence e-mail: wangwangzhaoyang@tom.com

There are two molecules in the asymmetric unit of title compound, C₁₁H₁₆BrNO₃, which was obtained via the tandem Michael addition-elimination reaction of 3,4-dibromo-5-methoxyfuran-2(5H)-one and 4-methylpiperidine in the presence of potassium fluoride. The furanone rings are approximately planar [maximum atomic deviations of 0.026 (2) and 0.015 (2) Å, respectively]. The packing is stabilized by weak intermolecular C-HO and C-HBr interactions.

Related literature

For biologically active 4-amino-2(5H)-furanones, see: Lattmann et al. (1999, 2005, 2006). For natural and synthetic products of 2(5H)-furanones, see: Zhou et al. (2009). For the synthesis of the title compound, see: Song, Wang et al. (2009). For a related structure, see Song, Li et al. (2009).

Experimental

Crystal data

C₁₁H₁₆BrNO₃
M_r = 290.15
Monoclinic, P 2₁ /c
a = 12.681 (3) Å
b = 10.481 (2) Å
c = 19.947 (4) Å
= 103.312 (3)°
V = 2579.9 (9) Å³
Z = 8
Mo K radiation
= 3.18 mm^-1
T = 298 K
0.32 × 0.22 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.436, T_max = 0.529
9692 measured reflections
4532 independent reflections
1918 reflections with I > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.109
S = 1.08
4532 reflections
294 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O2	0.98	2.56	3.486 (7)	157
C2-H2O6ⁱ	0.98	2.58	3.505 (7)	158
C2-H2Br1ⁱⁱ	0.98	3.06	3.718 (6)	126
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2228 ).

Acknowledgements

The work was supported by the National Natural Science Foundation of China (grant No. 20772035) and the Natural Science Foundation of Guangdong Province, China (grant No. 5300082).

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Lattmann, E., Billington, D. C. & Langley, C. A. (1999). Drug Des. Discov 16, 243-250.
Lattmann, E., Dunn, S., Niamsanit, S. & Sattayasai, N. (2005). Bioorg. Med. Chem. Lett. 15, 919-921.
Lattmann, E., Sattayasai, N., Schwalbe, C. S., Niamsanit, S., Billington, D. C., Lattmann, P., Langley, C. A., Singh, H. & Dunn, S. (2006). Curr. Drug Discov. Technol. 3, 125-134.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, X.-M., Li, Z.-Y., Wang, Z.-Y. & Fu, J.-H. (2009). Acta Cryst. E65, o1838.
Song, X.-M., Wang, Z.-Y., Fu, J.-H. & Li, J.-X. (2009). J. South China Normal Univ. (Nat. Sci. Ed.), 4, 75-80.
Zhou, L.-H., Yu, X.-Q. & Pu, L. (2009). J. Org. Chem. 74, 2013-2017.

organic compounds