(1E,4E)-1,5-Bis[2-(trifluoro­meth­yl)phen­yl]penta-1,4-dien-3-one

Park, D.H.; Ramkumar, V.; Parthiban, P.

doi:10.1107/S1600536812051586

Volume 69
Part 2
Page o177
February 2013

Received 25 November 2012
Accepted 21 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.037
wR = 0.096
Data-to-parameter ratio = 11.1
Details

(1E,4E)-1,5-Bis[2-(trifluoromethyl)phenyl]penta-1,4-dien-3-one

Dong Ho Park,^a V. Ramkumar ^b and P. Parthiban ^a ^*

^aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, and ^bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
Correspondence e-mail: parthisivam@yahoo.co.in

In the title compound, C₁₉H₁₂F₆O, a monoketone derivative of curcumin, both double bonds have a trans conformation. The molecule is mostly planar with all C and O atoms essentially coplanar, with the exception of one benzene ring, which is tilted by 17.18 (1)° with respect to the plane of the remainder of the molecule. The r.m.s. deviation from planarity of the coplanar section is 0.0097 Å. The crystal packing features weak C-HO and C-HF interactions.

Related literature

For the synthesis of chalcones, see: Tully et al. (2001). For the biological properties of chalcones, see: Buescher & Yang (2000); Kumar et al. (2003), Hsu & Cheng (2007). For their physical properties, see: Fichou et al. (1988); Butcher et al. (2006). For similar structures, see: Butcher et al. (2007); Nizam Mohideen et al. (2007); Harrison et al. (2006).

Experimental

Crystal data

C₁₉H₁₂F₆O
M_r = 370.29
Monoclinic, P c
a = 11.3123 (12) Å
b = 4.7907 (4) Å
c = 15.1697 (16) Å
= 101.834 (3)°
V = 804.63 (14) Å³
Z = 2
Mo K radiation
= 0.14 mm^-1
T = 298 K
0.35 × 0.25 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.952, T_max = 0.986
5185 measured reflections
2608 independent reflections
1931 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.096
S = 1.04
2608 reflections
235 parameters
2 restraints
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C17-H17F3ⁱ	0.93	2.62	3.399 (4)	141 (2)
C1-H1O1ⁱⁱ	0.93	2.72	3.290 (5)	121 (1)
Symmetry codes: (i) x-1, y-1, z; (ii) $[x, -y+2, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2522 ).

Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Buescher, R. & Yang, L. (2000). Turmeric in Natural Food Colorants, edited by G. J. Lauro & F. J. Francis, pp. 205-226. New York: Marcel Dekker.
Butcher, R. J., Jasinski, J. P., Sarojini, B. K., Yathirajan, H. S., Bindya, S. & Narayana, B. (2007). Acta Cryst. E63, o3213-o3214.
Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Mithun, A. (2006). Acta Cryst. E62, o1629-o1630.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Fichou, D., Watanabe, T., Takeda, T., Miyata, S., Goto, Y. & Nakayama, M. (1988). Jpn J. Appl. Phys. 27, 429-430.
Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. & Narayana, B. (2006). Acta Cryst. E62, o1522-o1523.
Hsu, C. H. & Cheng, A. L. (2007). Adv. Exp. Med. Biol. 595, 471-480.
Kumar, A. P., Aggarwal, B. B. & Bharti, A. C. (2003). Anticancer Res. 23, 363-398.
Nizam Mohideen, M., Thenmozhi, S., Subbiah Pandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4379.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tully, W., Main, L. & Nicholson, B. K. (2001). J. Organomet. Chem. 633, 162-172.

organic compounds