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

Srinivasan, T.; Senthilkumar, G.; Manikandan, H.; Gopalakrishanan, M.; Velmurugan, D.

doi:10.1107/S1600536813000032

Volume 69
Part 2
Page o215
February 2013

Received 17 December 2012
Accepted 2 January 2013
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.133
Data-to-parameter ratio = 18.5
Details

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

Thothadri Srinivasan,^a Govindaraj Senthilkumar,^b Haridoss Manikandan,^b Mannathusamy Gopalakrishanan ^b and Devadasan Velmurugan ^a ^*

^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, C₂₆H₂₂F₂O₂, the cyclopropane ring makes dihedral angles of 47.6 (2), 51.3 (2) and 63.9 (2)° with the 2-fluoro-substituted phenyl ring, the unsubstituted phenyl ring and the 4-fluoro-substituted phenyl ring, respectively. There is a short C-HF contact in the molecule. In the crystal, weak C-HF hydrogen bonds lead to chains of molecules extending along the b-axis direction.

Related literature

For the uses and biological importance of diketones, see: Bennett et al. (1999); Sato et al. (2008). For the crystal structure of a related compound, see: Li et al. (2008).

Experimental

Crystal data

C₂₆H₂₂F₂O₂
M_r = 404.44
Monoclinic, C 2/c
a = 38.9453 (14) Å
b = 5.7769 (2) Å
c = 18.3045 (7) Å
= 95.334 (2)°
V = 4100.4 (3) Å³
Z = 8
Mo K radiation
= 0.09 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) T_min = 0.972, T_max = 0.982
18721 measured reflections
5017 independent reflections
3326 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.133
S = 1.02
5017 reflections
271 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12F1ⁱ	0.98	2.51	3.402 (2)	151
C5-H5F1	0.98	2.42	2.833 (2)	105
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2615 ).

Acknowledgements

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

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.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Li, K.-Z., Chen, Y.-T., Zhao, C.-W., Wei, G.-D. & He, Q.-P. (2008). Acta Cryst. E64, o1665.
Sato, K., Yamazoe, S., Yamamoto, R., Ohata, S., Tarui, A., Omote, M., Kumadaki, I. & Ando, A. (2008). Org. Lett. 10, 2405-2408.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds