(IUCr) (E)-3-[4-(Pentyloxy)phenyl]-1-phenylprop-2-en-1-one

Volume 65
Part 6
Page o1280
June 2009

Received 28 April 2009
Accepted 4 May 2009
Online 14 May 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.101
Data-to-parameter ratio = 14.6
Details

(E)-3-[4-(Pentyloxy)phenyl]-1-phenylprop-2-en-1-one

Asghar Abbas,^a M. Khawar Rauf,^a Michael Bolte ^b and Aurangzeb Hasan ^a ^*

^aDepartment of Chemistry, Quaid-i-Azam University Islamabad, 45320-Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: flavonoids@hotmail.com

The title compound, C₂₀H₂₂O₂, crystallizes with two independent molecules in the asymmetric unit. In each molecule, all the non-H atoms lie in a common plane (r.m.s. deviations of 0.098 and 0.079 Å). There is a [pi] - [pi] stacking interaction in the crystal structure. The central aromatic rings of the two molecules, which are stacked head-to-tail one above the other, are separated by centroid-to-centroid distances of 3.872 (13) and 3.999 (10) Å.

Related literature

For background information on chalcones and their properties, see: Achanta et al. (2006); Zhang et al. (2009); Tran et al. (2009); Yagura et al. (2008); Sarissky et al. (2008); Tang et al. (2008); Srivastava et al. (2008); For bond-length data, see: Allen et al. (1987). For related structures, see: Rosli et al. (2006); Harrison et al. (2006). For the synthesis, see: Wattanasin & Murphy (1980).

Experimental

Crystal data

C₂₀H₂₂O₂
M_r = 294.38
Monoclinic, P 2₁ /c
a = 7.4881 (4) Å
b = 21.3067 (11) Å
c = 20.8328 (11) Å
= 93.974 (4)°
V = 3315.8 (3) Å³
Z = 8
Mo K radiation
= 0.07 mm^-1
T = 173 K
0.38 × 0.22 × 0.22 mm

Data collection

Stoe IPDS II two-circle-diffractometer
Absorption correction: none
25934 measured reflections
5819 independent reflections
3319 reflections with I > 2(I)
R_int = 0.086

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.101
S = 0.82
5819 reflections
398 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.19 e Å^-3

Table 1
Selected torsion angles (°)

C11-C1-C2-C3	-177.21 (17)
C2-C1-C11-C12	-13.4 (3)
C2-C1-C11-C16	167.85 (17)
C11A-C1A-C2A-C3A	-170.05 (18)
C2A-C1A-C11A-C12A	-9.5 (3)
C2A-C1A-C11A-C16A	171.52 (17)

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2111 ).

Acknowledgements

AA is grateful to the Higher Education Commission of Pakistan for financial support for his PhD program under scholarship No. IIC-0317109.

References

Achanta, G., Modzelewska, A., Feng, L., Khan, S. R. & Huang, P. (2006). Mol. Pharmacol. 70, 426-433.
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.
Harrison, W. T. A., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Vijaya Raj, K. K. (2006). Acta Cryst. E62, o1578-o1579.
Rosli, M. M., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1466-o1468.
Sarissky, M., Pilatova, M., Perjesi, P., Mojzis, J. & Sulla, I. (2008). Neuro Oncology. 10, 1112-1112.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Srivastava, S. S., Joshi, S., Singh, A. R., Yadav, S., Saxena, A. S., Ram, V. J., Chandra, S. & Saxena, J. K. (2008). Med. Chem. Res. 17, 234-244.
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.
Tang, Y. X., Simoneau, A. R., Xie, J., Shahandeh, B. & Zi, X. L. (2008). Cancer Prevent. Res. 1, 439-451.
Tran, T. D., Park, H., Kim, H. P., Ecker, G. F. & Thai, K. M. (2009). Bioorg. Med. Chem. Lett. 19, 1650-1653.
Wattanasin, S. & Murphy, W. S. (1980). Synthesis, 647-650.
Yagura, T., Motomiya, T., Ito, M., Honda, G., Iida, A., Kiuchi, F., Tokuda, H. & Nishino, H. (2008). J. Nat. Med. 62, 174-178.
Zhang, X. D., Hu, X., Hou, A. J. & Wang, H. Y. (2009). Biol. Pharm. Bull. 32, 86-90.

organic compounds