(2E)-1-(2,6-Dichloro-3-fluoro­phen­yl)-3-phenyl­prop-2-en-1-one

Aletti S Praveen; Hemmige S Yathirajan; Badiadka Narayana; Thomas Gerber; Eric Hosten; Richard Betz

doi:10.1107/S1600536812010574

. 2012 Mar 17;68(Pt 4):o1085. doi: 10.1107/S1600536812010574

(2E)-1-(2,6-Dichloro-3-fluorophenyl)-3-phenylprop-2-en-1-one

Aletti S Praveen ^a, Hemmige S Yathirajan ^a, Badiadka Narayana ^b, Thomas Gerber ^c, Eric Hosten ^c, Richard Betz ^c,^*

PMCID: PMC3344040 PMID: 22589949

Abstract

In the title compound, C₁₅H₉Cl₂FO, the F atom shows positional disorder over two positions, with site-occupancy factors of 0.747 (4) and 0.253 (4). The dihedral angle between the rings is 86.37 (10)°. In the crystal, C—H⋯O contacts connect the molecules into chains along the c axis. The shortest inter-centroid distance between two aromatic systems is 3.6686 (12) Å and is apparent between the halogenated rings.

Related literature

For pharmaceutical background to chalcones, see: Lin et al. (2002 ▶); Modzelewska et al. (2006 ▶); Svetaz et al. (2004 ▶). For related structures, see: Betz et al. (2012 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₉Cl₂FO
M _r = 295.12
Monoclinic,
a = 11.3390 (3) Å
b = 10.3896 (3) Å
c = 11.3930 (3) Å
β = 97.078 (1)°
V = 1331.95 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 200 K
0.49 × 0.34 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.798, T _max = 0.920
23002 measured reflections
3329 independent reflections
2742 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.111
S = 1.04
3329 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); 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, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010574/hg5184sup1.cif

e-68-o1085-sup1.cif^{(21.7KB, cif)}

Supplementary material file. DOI: 10.1107/S1600536812010574/hg5184Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010574/hg5184Isup3.hkl

e-68-o1085-Isup3.hkl^{(163.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010574/hg5184Isup4.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
C1—H1⋯O1ⁱ	0.95	2.50	3.399 (2)	158
C16—H16⋯O1ⁱ	0.95	2.57	3.440 (2)	153

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Symmetry code: (i) Inline graphic .

Acknowledgments

ASP thanks the University of Mysore for research facilities.

supplementary crystallographic information

Comment

Substituted chalcones and their derivatives have been reported to possess interesting biological properties such as being antitubercular (Lin et al., 2002), anticancer (Modzelewska et al., 2006) and antifungal agents (Svetaz et al., 2004). The crystal structures of some chalcones such as (2E)-1-(2,6-Dichloro-3-fluorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (Betz et al., 2012) have been reported in the literature. As part of our ongoing studies on chalcones, the title compound was synthesized and characterized by X-ray diffraction.

The fluorine atom on the halogenated phenyl ring shows rotational disorder over two positions with site occupancy factors of 0.75 and 0.25. The least-squares planes defined by the carbon atoms of the two aromatic moieties intersect at an angle of 86.37 (10)° (Fig. 1).

In the crystal, C–H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the respective atoms are present. These are supported by one of the vinylic hydrogen atoms and one of the hydrogen atoms of the unsubstituted phenyl ring. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for the hydrogen bonds is C¹₁(5)C¹₁(7) on the unary level. Metrical information about these contacts as well as their symmetry is summarized in Table 1. In total, the molecules are connected to chains along the crystallographic c axis. The shortest intercentroid distance between two aromtic systems was measured at 3.6686 (12) Å and is apparent between the halogenated phenyl rings (Fig. 2).

The packing of the title compound in the crystal structure is shown in Figure 3.

Experimental

To a stirred solution of 1-(2,6-dichloro-3-fluorophenyl)ethanone (1 g, 4.8 mmol) and benzaldehyde (0.51 g, 4.8 mmol) in ethanol (10 ml), powdered KOH (0.40 g 7.2 mmol) was added at 0 °C. The reaction mixture was stirred at room temperature for 2 h. After completion of the reaction, the mixture was pourred into ice cold water and subsequently acidified with 1.5 N HCl (pH ~3). The precipitated solid was filtered and dried to afford 1.2 g of the title compound as off-white solid in 86% yield. The single-crystal was grown from a mixture of toluene:acetone (v:v = 1:1) by slow evaporation at room temperature (m.p.: 385–388 K).