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Volume 68 
Part 12 
Pages o3433-o3434  
December 2012  

Received 16 October 2012
Accepted 14 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.089
Data-to-parameter ratio = 18.4
Details
Open access

(2E)-3-(4-Bromophenyl)-1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl)prop-2-en-1-one

aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India,bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C28H19BrF2O2, the C=C double bond is E-configured. In the crystal, C-H...O and C-H...F contacts connect molecules into planes perpendicular to the c axis. The shortest centroid-centroid distance between two aromatic systems is 3.6745 (12) Å between one of the para-fluorophenyl rings and its symmetry-generated equivalent.

Related literature

For background to polysubstituted aromatics, see: Astrue (2002[Astrue, D. (2002). In Modern Arene Chemistry. Weinheim: Wiley-VCH.]). For the pharmacological properties of terphenyls, see: Liu (2006[Liu, J. K. (2006). Chem. Rev. 106, 2209-2223.]). For the crystal structures of various terphenyl chalcones, see: Fun et al. (2012a[Fun, H.-K., Loh, W.-S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2024.],b[Fun, H.-K., Loh, W.-S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o1877-o1878.],c[Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012c). Acta Cryst. E68, o1560-o1561.],d[Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012d). Acta Cryst. E68, o1314-o1315.],e[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012e). Acta Cryst. E68, o163.]); Betz et al. (2011a[Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o3323-o3324.],b[Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o3159-o3160.],c[Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011c). Acta Cryst. E67, o3181-o3182.],d[Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011d). Acta Cryst. E67, o3179-o3180.],e[Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011e). Acta Cryst. E67, o2996-o2997.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C28H19BrF2O2

  • Mr = 505.34

  • Triclinic, [P \overline 1]

  • a = 6.9648 (2) Å

  • b = 11.3616 (3) Å

  • c = 14.7219 (4) Å

  • [alpha] = 95.983 (1)°

  • [beta] = 92.601 (1)°

  • [gamma] = 105.676 (1)°

  • V = 1112.23 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.89 mm-1

  • T = 200 K

  • 0.39 × 0.18 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.]) Tmin = 0.843, Tmax = 1.000

  • 20205 measured reflections

  • 5513 independent reflections

  • 4082 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.089

  • S = 1.03

  • 5513 reflections

  • 299 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.59 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4B...F1i 0.98 2.51 3.428 (2) 156
C25-H25...O1ii 0.95 2.43 3.268 (2) 147
Symmetry codes: (i) x+1, y+1, z; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2214 ).


Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

References

Astrue, D. (2002). In Modern Arene Chemistry. Weinheim: Wiley-VCH.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011e). Acta Cryst. E67, o2996-o2997.  [CSD] [CrossRef] [details]
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o3323-o3324.  [CSD] [CrossRef] [details]
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o3159-o3160.  [CSD] [CrossRef] [details]
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011c). Acta Cryst. E67, o3181-o3182.  [CSD] [CrossRef] [details]
Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011d). Acta Cryst. E67, o3179-o3180.  [CSD] [CrossRef] [details]
Bruker (2008). SADABS. Bruker Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012c). Acta Cryst. E68, o1560-o1561.  [CSD] [CrossRef] [details]
Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012d). Acta Cryst. E68, o1314-o1315.  [CSD] [CrossRef] [details]
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012e). Acta Cryst. E68, o163.  [CSD] [CrossRef] [details]
Fun, H.-K., Loh, W.-S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2024.  [CSD] [CrossRef] [details]
Fun, H.-K., Loh, W.-S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o1877-o1878.  [CSD] [CrossRef] [details]
Liu, J. K. (2006). Chem. Rev. 106, 2209-2223.  [ISI] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3433-o3434   [ doi:10.1107/S1600536812046831 ]

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