2-(4-Bromo­phen­oxy)-3-isopropyl-5,6,7,8-tetra­hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

Wang, H.-M.; Chen, L.-L.; Hu, T.; Zeng, X.-H.

doi:10.1107/S160053680803732X

Volume 64
Part 12
Page o2404
December 2008

Received 9 November 2008
Accepted 11 November 2008
Online 22 November 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.014 Å
R = 0.067
wR = 0.204
Data-to-parameter ratio = 14.2
Details

2-(4-Bromophenoxy)-3-isopropyl-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one

Hong-Mei Wang,^a Li-Li Chen,^a Ting Hu ^a and Xiao-Hua Zeng ^a ^*

^aDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China
Correspondence e-mail: zengken@126.com

In the title compound, C₁₉H₁₉BrN₂O₂S, the central thienopyrimidine ring system is essentially planar, with a maximum displacement of 0.068 (3) Å. The attached cyclohexene ring adopts a half-chair conformation. The molecular conformation and crystal packing are stabilized by three intramolecular C-HO hydrogen bonds and two C-H [pi] interactions.

Related literature

For background to the use of pyrimidine derivatives as drugs, see: Ding et al. (2004). For a description of the Cambridge Structural Database, see: Allen (2002). For a related structure, see: Zeng et al. (2006).

Experimental

Crystal data

C₁₉H₁₉BrN₂O₂S
M_r = 418.32
Monoclinic, P 2₁
a = 13.3957 (7) Å
b = 5.7366 (3) Å
c = 13.3956 (7) Å
= 115.5410 (10)°
V = 928.81 (8) Å³
Z = 2
Mo K radiation
= 2.34 mm^-1
T = 298 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.652, T_max = 0.800
5798 measured reflections
3228 independent reflections
2346 reflections with I > 2(I)
R_int = 0.106

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.204
S = 1.07
3228 reflections
228 parameters
1 restraint
H-atom parameters constrained
_max = 7.69 e Å^-3
_min = -2.63 e Å^-3
Absolute structure: Flack (1983), 1424 Freidel pairs
Flack parameter: 0.00 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O1	0.98	2.20	2.726 (10)	112
C12-H12BO2	0.96	2.43	2.915 (13)	111
C13-H13AO2	0.96	2.38	2.951 (10)	117
C12-H12ACg1ⁱ	0.96	2.92	3.854 (11)	165
C12-H12ACg2ⁱ	0.96	2.71	3.434 (11)	133
Symmetry code: (i) x, y-1, z. Cg1 and Cg2 are the centroids of the thiophene (S1/C5-C8) and pyrimidine (N1/N2/C7-C10) rings, respectively.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2674 ).

Acknowledgements

We gratefully acknowledge financial support of this work by the Research Foundation for Students and Teachers of Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem. 69, 8366-8371.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Zeng, X.-H., Ding, M.-W. & He, H.-W. (2006). Acta Cryst. E62, o731-o732.

organic compounds