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Volume 69 
Part 2 
Page o252  
February 2013  

Received 4 January 2013
Accepted 11 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.146
Data-to-parameter ratio = 19.6
Details
Open access

5-(4-Chlorophenyl)-1-cyclopropyl-2-(2-fluorophenyl)-3-phenylpentane-1,5-dione

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Tamilnadu, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C26H22ClFO2, the cyclopropane ring makes dihedral angles of 45.7 (2), 49.0 (2) and 65.2 (2)° with the fluoro-substituted phenyl ring, the benzene ring and the chloro-substituted phenyl ring, respectively. The F and Cl atoms deviate by 0.0307 (11) and 0.0652 (6) Å, respectively, from the planes of the phenyl rings to which they are attached. In the crystal, molecules are linked by C-H...F hydrogen bonds, forming chains along the b axis.

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999[Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.]); Sato et al. (2008[Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405-2408.]). For a related structure, see: Li et al. (2008[Li, K.-Z., Chen, Y.-T., Zhao, C.-W., Wei, G.-D. & He, Q.-P. (2008). Acta Cryst. E64, o1665.]).

[Scheme 1]

Experimental

Crystal data
  • C26H22ClFO2

  • Mr = 420.89

  • Monoclinic, C 2/c

  • a = 43.0465 (15) Å

  • b = 5.7257 (2) Å

  • c = 18.2828 (6) Å

  • [beta] = 109.103 (2)°

  • V = 4258.0 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.940, Tmax = 0.960

  • 20606 measured reflections

  • 5308 independent reflections

  • 3857 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.146

  • S = 1.02

  • 5308 reflections

  • 271 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...F1i 0.98 2.54 3.433 (2) 151
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: SU2549 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS also thanks the DST for an Inspire fellowship.

References

Bennett, I., Broom, N. J. P., Cassels, R., Elder, J. S., Masson, N. D. & O'Hanlon, P. J. (1999). Bioorg. Med. Chem. Lett. 9, 1847-1852.  [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Li, K.-Z., Chen, Y.-T., Zhao, C.-W., Wei, G.-D. & He, Q.-P. (2008). Acta Cryst. E64, o1665.  [CSD] [CrossRef] [details]
Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405-2408.  [ISI] [CrossRef] [PubMed] [ChemPort]
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 (2013). E69, o252  [ doi:10.1107/S1600536813001074 ]

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