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

Srinivasan, T.; Senthilkumar, G.; Manikandan, H.; Neelakandan, K.; Velmurugan, D.

doi:10.1107/S1600536813001074

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.146
Data-to-parameter ratio = 19.6
Details

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

Thothadri Srinivasan,^a Govindaraj Senthilkumar,^b Haridoss Manikandan,^b Kaliaperumal Neelakandan ^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, 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-HF hydrogen bonds, forming chains along the b axis.

Related literature

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

Experimental

Crystal data

C₂₆H₂₂ClFO₂
M_r = 420.89
Monoclinic, C 2/c
a = 43.0465 (15) Å
b = 5.7257 (2) Å
c = 18.2828 (6) Å
= 109.103 (2)°
V = 4258.0 (3) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.940, T_max = 0.960
20606 measured reflections
5308 independent reflections
3857 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.146
S = 1.02
5308 reflections
271 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12F1ⁱ	0.98	2.54	3.433 (2)	151
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 for Windows (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: 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.
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