Ethyl 4-(4-bromo­phen­yl)-6-(4-ethoxy­phen­yl)-2-oxocyclo­hex-3-enecarboxyl­ate

Badshah, A.; Hasan, A.; Barbarín, C.R.

doi:10.1107/S1600536809003523

Volume 65
Part 3
Page o467
March 2009

Received 27 December 2008
Accepted 28 January 2009
Online 6 February 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R = 0.059
wR = 0.175
Data-to-parameter ratio = 14.3
Details

Ethyl 4-(4-bromophenyl)-6-(4-ethoxyphenyl)-2-oxocyclohex-3-enecarboxylate

Amir Badshah,^a Aurangzeb Hasan ^a ^* and Cecilia R. Barbarín ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDivisión de Estudios de Posgrado, Facultad de Ciencias Químicas, UANL, Guerreo y Progreso S/N, Col. Treviño, CP, 64570 Monterrey, NL, Mexico
Correspondence e-mail: h.aurangzeb@yahoo.com

The title compound, C₂₃H₂₃BrO₄, is an intermediate in the synthesis of fused heterocycles. In the title molecule, the cyclohexene ring has a distorted half-chair conformation. The bromophenyl ring and the mean plane of the cyclohexene ring form a dihedral angle of 13.8 (3)°, whereas the benzene and cyclohexene rings are approximately perpendicular [88.44 (17)°]. There are only weak C-HO and C-H [pi] intermolecular interactions.

Related literature

For applications of cyclohexenones, see: Eddington et al. (2000); Li & Strobel (2001); Luu et al. (2000); Padmavathi et al. (2000, 2001).

Experimental

Crystal data

C₂₃H₂₃BrO₄
M_r = 443.32
Monoclinic, P 2₁ /c
a = 12.792 (4) Å
b = 14.537 (4) Å
c = 12.114 (4) Å
= 113.88 (2)°
V = 2059.8 (11) Å³
Z = 4
Mo K radiation
= 2.02 mm^-1
T = 298 (2) K
0.50 × 0.50 × 0.08 mm

Data collection

Bruker P4 diffractometer
Absorption correction: gaussian (XSCANS; Bruker, 1999) T_min = 0.246, T_max = 0.941
7765 measured reflections
3630 independent reflections
2088 reflections with I > 2(I)
R_int = 0.054
3 standard reflections every 97 reflections intensity decay: 6.4%

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.175
S = 1.01
3630 reflections
254 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5AO1ⁱ	0.93	2.42	3.163 (6)	137
C8-H8AO2ⁱⁱ	0.97	2.59	3.244 (6)	125
C15-H15BO2	0.96	2.58	3.062 (13)	111
C23-H23ACgⁱⁱⁱ	0.96	2.90	3.741 (6)	147
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL-Plus.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2184 ).

Acknowledgements

AB is grateful to the Higher Education Commission of Pakistan for a PhD scholarship.

References

Bruker (1999). XSCANS Users Manual. Bruker AXS Inc., Madison, Wisconsin, USA.
Eddington, N. D., Cox, D. S., Roberts, R. R., Stables, J. P., Powell, C. B. & Scott, A. R. (2000). Curr. Med. Chem. 7, 417-436.
Li, J. Y. & Strobel, G. A. (2001). Phytochemistry, 57, 261-265.
Luu, B., Aguilar, J. L. G. D. & Junges, C. G. (2000). Molecules, 5, 1439-1460.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Padmavathi, V., Reddy, B. J. M., Balaiah, A., Reddy, K. V. & Reddy, D. B. (2000). Molecules, 5, 1281-1286.
Padmavathi, V., Sharmila, K., Reddy, A. S. & Reddy, D. B. (2001). Indian J. Chem. Sect. B, 40, 11-14.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds