(E)-3-[4-(Dimethyl­amino)phen­yl]-1-(4-methyl­phen­yl)prop-2-en-1-one

Wang, L.; Ma, L.-Y.; Huang, Y.-L.; Zheng, B.-Y.

doi:10.1107/S1600536809052398

Volume 66
Part 1
Page o174
January 2010

Received 22 November 2009
Accepted 5 December 2009
Online 16 December 2009

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.004 Å
R = 0.061
wR = 0.136
Data-to-parameter ratio = 10.6
Details

(E)-3-[4-(Dimethylamino)phenyl]-1-(4-methylphenyl)prop-2-en-1-one

Lei Wang,^a ^* Li-Ying Ma,^a Yu-Ling Huang ^a and Bai-Yu Zheng ^a

^aBinzhou Medical University, Yantai 264003, People's Republic of China
Correspondence e-mail: wanglei424@163.com

In the title compound, C₁₈H₁₉NO, the dihedral angle between 4-methylphenyl and 4-(dimethylamino)phenyl rings is 45.5 (3)°. The C-C=C-C torsion angle of 173.8 (3)° indicates that the molecule adopts an E configuration. The dimethylamino group is nearly coplanar with the attached benzene ring, making a dihedral angle of 2.7 (3)°. Weak intermolecular C-H [pi] interactions are observed in the crystal structure.

Related literature

The title compound is a chalcone derivative; for the biological activiy of chalcones, see: Modzelewska et al. (2006); Opletalova & Sedivy (1999); Lin et al. (2002); Hsieh et al. (1998); Lunardi et al. (2003); Tang et al. (2008). For the organic non-linear optical properties of chalcones, see: Indira et al. (2002); Ravindra et al. (2009). For related structures, see: Wang et al. (2004); Yang et al. (2006).

Experimental

Crystal data

C₁₈H₁₉NO
M_r = 265.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.276 (2) Å
b = 11.567 (3) Å
c = 17.642 (5) Å
V = 1484.8 (7) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 193 K
0.59 × 0.35 × 0.18 mm

Data collection

Rigaku Mercury diffractometer
16704 measured reflections
1958 independent reflections
1846 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.136
S = 1.31
1958 reflections
185 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C7-C11 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C11-H11Cg1ⁱ	0.95	2.94	3.697 (3)	138
C9-H9Cg2ⁱⁱ	0.95	2.93	3.712 (3)	141
C16-H16BCg2ⁱⁱⁱ	0.98	2.70	3.643 (3)	161
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[-x+{\script{5\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (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: XU2690 ).

Acknowledgements

The authors are grateful to Binzhou Medical University for financial support (grant No. BY2007KJ57).

References

Hsieh, H. K., Lee, T. H., Wang, J. P., Wang, J. J. & Lin, C. N. (1998). Pharm. Res. 15, 39-46.
Indira, J., Prakash Karat, P. & Sarojini, B. K. (2002). J. Cryst. Growth, 242, 209-214.
Lin, Y. M., Zhou, Y., Flavin, M. T., Zhou, L. M., Nie, W. & Chen, F. C. (2002). Bioorg. Med. Chem. 10, 2795-2802.
Lunardi, F., Guzela, M., Rodrigues, A. T., Correa, R., Eger-Mangrich, I., Steindel, M., Grisard, E. C., Assreuy, J., Calixto, J. B. & Santos, A. R. S. (2003). Antimicrob. Agents Chemother. 47, 1449-1451.
Modzelewska, A., Pettit, C., Achanta, G., Davidson, N. E., Huang, P. & Khan, S. R. (2006). Bioorg. Med. Chem. 14, 3491-3495.
Opletalova, V. & Sedivy, D. (1999). Ceska Slov. Farm. 48, 252-255.
Ravindra, H. J., Harrison, W. T., Suresh Kumar, M. R. & Dharmaprakash, S. M. (2009). J. Cryst. Growth, 311, 310-315.
Rigaku (1999). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2000). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tang, S.-P., Kuang, D.-Z., Feng, Y.-L., Li, W. & Chen, Z.-M. (2008). Acta Cryst. E64, o1123.
Wang, L., Zhang, Y., Lu, C.-R. & Zhang, D.-C. (2004). Acta Cryst. C60, o696-o698.
Yang, W., Wang, L. & Zhang, D.-C. (2006). J. Chem. Crystallogr. 36, 195-198.

organic compounds