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

Thothadri Srinivasan; Govindaraj Senthilkumar; Haridoss Manikandan; Kaliaperumal Neelakandan; Devadasan Velmurugan

doi:10.1107/S1600536813001074

. 2013 Jan 19;69(Pt 2):o252. doi: 10.1107/S1600536813001074

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, Devadasan Velmurugan ^a,^*

PMCID: PMC3569784 PMID: 23424530

Abstract

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 ▶); Sato et al. (2008 ▶). For a related structure, see: Li et al. (2008 ▶).

Experimental

Crystal data

C₂₆H₂₂ClFO₂
M _r = 420.89
Monoclinic,
a = 43.0465 (15) Å
b = 5.7257 (2) Å
c = 18.2828 (6) Å
β = 109.103 (2)°
V = 4258.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.146
S = 1.02
5308 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.41 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(22.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001074/su2549sup1.cif

e-69-0o252-sup1.cif^{(22.3KB, cif)}

Click here for additional data file.^{(254.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001074/su2549Isup2.hkl

e-69-0o252-Isup2.hkl^{(254.8KB, hkl)}

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

Supplementary material file. DOI: 10.1107/S1600536813001074/su2549Isup3.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	2.54	3.433 (2)	151

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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 also thanks the DST for an Inspire fellowship.

supplementary crystallographic information

Comment

Diketones are popular in organic synthesis for their applications in biology and medicine. They are known to exhibit antioxidant, antitumour and antibacterial activities (Bennett et al., 1999). They are also key intermediates in the preparation of various heterocyclic compounds (Sato et al., 2008). We report herein on the synthesis and crystal structure of one the title diketone.

In the title compound, Fig.1, the cyclopropane ring (C1-C3) makes a dihedral angle of 45.7 (2)° with the fluoro substituted phenyl ring (C6-C11). It makes a dihedral angle of 49.0 (2)° with the unsubstituted phenyl ring (C13-C18) and a dihedral angle of 65.2 (2)° with the chloro substituted phenyl ring (C21-C26). The fluorine atom, F1, deviates by 0.0307 (11) Å from the phenyl ring to which it is attached.

The dihedral angle between the unsubstituted phenyl ring and the fluoro substituted phenyl ring is 3.65 (8)° and the dihedral angle between the unsubstituted phenyl ring and the chloro substituted phenyl ring is 71.73 (8)°. The dihedral angle between the fluoro substituted phenyl ring and the chloro substituted phenyl ring is 71.15 (8)°. The chloro atom, Cl1, deviates by 0.0652 (6) Å from the phenyl ring to which it is attached.

In the crystal, C–H···F hydrogen bonds link the molecules to form chains along the b axis (Table 1 and Fig. 2).

Experimental

A mixture of 4-chloroacetophenone(0.01mole), 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 [Yield = 95%, M.p. = 405 - 407 K] giving block-like colourless crystals of the title compound.