(E)-3-(2,4-Dimeth­oxy­phen­yl)-1-(3,4-dimeth­oxy­phen­yl)prop-2-en-1-one

Wu, X.; Cai, X.; Zheng, X.; Zhang, Z.; Ye, X.

doi:10.1107/S1600536810043606

Volume 66
Part 11
Page o3015
November 2010

Received 17 September 2010
Accepted 26 October 2010
Online 31 October 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 13.4
Details

(E)-3-(2,4-Dimethoxyphenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

Xiaokai Wu,^a Xiaoqing Cai,^b Xianan Zheng,^a Zhennan Zhang ^a and Xiaoqin Ye ^a ^*

^aSchool of Pharmacy, Wenzhou Medical College, Wenzhou, Zhejiang 325035, People's Republic of China, and ^bCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, People's Republic of China
Correspondence e-mail: wujianzhang6@163.com

The title compound, C₁₉H₂₀O₅, is approximately planar; the dihedral angle between the benzene rings is 3.82 (8)°, and the central propenone C(=O)-C=C plane makes dihedral angles of 1.95 (10) and 3.17 (11)° with the two benzene rings. In the crystal structure, intra- and intermolecular C-HO hydrogen bonds are observed.

Related literature

For related structures, see: Huang et al. (2010); Peng et al. (2010); Yathirajan et al. (2006); Zhao et al. (2010). For background to and applications of chalcones, see: Liang et al. (2007); Liu et al. (2008); Mojzisa et al. (2008); Nielsen et al. (2005); Nowakowska (2007); Selvakumar et al. (2007); Wu et al. (2010); Wu, Chen et al. (2009); Wu, Qiu et al. (2009); Wu, Zhang et al. (2009).

Experimental

Crystal data

C₁₉H₂₀O₅
M_r = 328.35
Monoclinic, P 2₁ /n
a = 9.031 (5) Å
b = 7.962 (5) Å
c = 23.631 (14) Å
= 92.827 (10)°
V = 1697.0 (17) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.47 × 0.35 × 0.31 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.958, T_max = 0.972
8581 measured reflections
2981 independent reflections
2407 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.119
S = 1.04
2981 reflections
222 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O3ⁱ	0.93	2.46	3.363 (3)	162
C8-H8BO4ⁱⁱ	0.96	2.60	3.537 (3)	166
C10-H10O2	0.93	2.25	2.846 (3)	121
C19-H19AO1ⁱⁱⁱ	0.96	2.54	3.443 (3)	157
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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: IS2604 ).

Acknowledgements

The authors acknowledge financial support from the Scientific Research Fund of Zhejiang Provincial Education Department (grant No. Y200907137).

References

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organic compounds