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

Thothadri Srinivasan; Govindaraj Senthilkumar; Haridoss Manikandan; Mannathusamy Gopalakrishanan; Devadasan Velmurugan

doi:10.1107/S1600536813000032

. 2013 Jan 9;69(Pt 2):o215. doi: 10.1107/S1600536813000032

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, Devadasan Velmurugan ^a,^*

PMCID: PMC3569750 PMID: 23424496

Abstract

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—H⋯F contact in the molecule. In the crystal, weak C—H⋯F 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,
a = 38.9453 (14) Å
b = 5.7769 (2) Å
c = 18.3045 (7) Å
β = 95.334 (2)°
V = 4100.4 (3) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.133
S = 1.02
5017 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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 Material

Click here for additional data file.^{(29.5KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000032/pv2615sup1.cif

e-69-0o215-sup1.cif^{(29.5KB, cif)}

Click here for additional data file.^{(240.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000032/pv2615Isup2.hkl

e-69-0o215-Isup2.hkl^{(240.8KB, hkl)}

Click here for additional data file.^{(7.7KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000032/pv2615Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯F1ⁱ	0.98	2.51	3.402 (2)	151
C5—H5⋯F1	0.98	2.42	2.833 (2)	105

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Symmetry code: (i) Inline graphic .

Acknowledgments

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.

supplementary crystallographic information

Comment

Diketones are popular in organic synthesis for their applications in biology and medicine. They are known to exhibit antioxidants, antitumour and antibacterial activities (Bennett et al.,1999). They are also key intermediates in the preparation of various heterocyclic compounds (Sato et al., 2008).

In the titled compound (Fig.1), the cyclopropane ring (C1/C2/C3) makes a dihedral angle of 47.6 (2)° with the fluoro substituted phenyl ring (C6/C7/C8/C9/C10/C11). It makes a dihedral angle of 51.3 (2)° with the unsubstituted phenyl ring (C13/C14/C15/C16/C17/C18) and a dihedral angle of 63.9 (2)° with the fluoro substituted phenyl ring (C21/C22/C23/C24/C25/C26). The dihedral angle between the unsubstituted phenyl ring and the fluoro substituted phenyl ring (C6–C11) is 3.86 (9)° and the dihedral angle between the unsubstituted phenyl ring and the fluoro substituted phenyl ring (C21–C26) is 69.43 (9)°. The dihedral angle between the two fluoro substituted phenyl rings is 67.28 (9)°. The packing of the crystal is stabilized by weak C–H···F hydrogen bonding interactions (Tab. 1 & Fig. 2).

Experimental

A mixture of 4-fluoroacetophenone (0.01 mole), benzaldehyde (0.01 mole), cyclopropyl 2-fluorobenzyl ketone (0.01 mole) and sodium hydroxide solution (10 ml, 10%) in ethanol (50 ml) was stirred for 3 hrs at room temperature. The solid that separated was filtered and washed with distilled water. The product was recrystallised from ethanol to yield the crystals of the title compound suitable for X-ray crystallographic studies. Yield = 97%, melting point = 391–393 K.