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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 [sigma](C-C) = 0.004 Å
R = 0.037
wR = 0.096
Data-to-parameter ratio = 11.1
Details
Open access

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

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-H...O and C-H...F interactions.

Related literature

For the synthesis of chalcones, see: Tully et al. (2001[Tully, W., Main, L. & Nicholson, B. K. (2001). J. Organomet. Chem. 633, 162-172.]). For the biological properties of chalcones, see: Buescher & Yang (2000[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.]); Kumar et al. (2003[Kumar, A. P., Aggarwal, B. B. & Bharti, A. C. (2003). Anticancer Res. 23, 363-398.]), Hsu & Cheng (2007[Hsu, C. H. & Cheng, A. L. (2007). Adv. Exp. Med. Biol. 595, 471-480.]). For their physical properties, see: Fichou et al. (1988[Fichou, D., Watanabe, T., Takeda, T., Miyata, S., Goto, Y. & Nakayama, M. (1988). Jpn J. Appl. Phys. 27, 429-430.]); Butcher et al. (2006[Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Mithun, A. (2006). Acta Cryst. E62, o1629-o1630.]). For similar structures, see: Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Sarojini, B. K., Yathirajan, H. S., Bindya, S. & Narayana, B. (2007). Acta Cryst. E63, o3213-o3214.]); Nizam Mohideen et al. (2007[Nizam Mohideen, M., Thenmozhi, S., Subbiah Pandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4379.]); Harrison et al. (2006[Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. & Narayana, B. (2006). Acta Cryst. E62, o1522-o1523.]).

[Scheme 1]

Experimental

Crystal data
  • C19H12F6O

  • Mr = 370.29

  • Monoclinic, P c

  • a = 11.3123 (12) Å

  • b = 4.7907 (4) Å

  • c = 15.1697 (16) Å

  • [beta] = 101.834 (3)°

  • V = 804.63 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.986

  • 5185 measured reflections

  • 2608 independent reflections

  • 1931 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.096

  • S = 1.04

  • 2608 reflections

  • 235 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17...F3i 0.93 2.62 3.399 (4) 141 (2)
C1-H1...O1ii 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[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]; 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.  [CSD] [CrossRef] [details]
Butcher, R. J., Yathirajan, H. S., Sarojini, B. K., Narayana, B. & Mithun, A. (2006). Acta Cryst. E62, o1629-o1630.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fichou, D., Watanabe, T., Takeda, T., Miyata, S., Goto, Y. & Nakayama, M. (1988). Jpn J. Appl. Phys. 27, 429-430.  [CrossRef]
Harrison, W. T. A., Sarojini, B. K., Vijaya Raj, K. K., Yathirajan, H. S. & Narayana, B. (2006). Acta Cryst. E62, o1522-o1523.  [CSD] [CrossRef] [details]
Hsu, C. H. & Cheng, A. L. (2007). Adv. Exp. Med. Biol. 595, 471-480.  [CrossRef] [PubMed]
Kumar, A. P., Aggarwal, B. B. & Bharti, A. C. (2003). Anticancer Res. 23, 363-398.  [PubMed]
Nizam Mohideen, M., Thenmozhi, S., Subbiah Pandi, A., Murugan, R. & Narayanan, S. S. (2007). Acta Cryst. E63, o4379.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tully, W., Main, L. & Nicholson, B. K. (2001). J. Organomet. Chem. 633, 162-172.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o177  [ doi:10.1107/S1600536812051586 ]

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