organic compounds
(2E)-1-(2,6-Dichloro-3-fluorophenyl)-3-phenylprop-2-en-1-one
aUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, bMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, and cNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth 6031, South Africa
*Correspondence e-mail: richard.betz@webmail.co.za
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 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).
see: LinExperimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2010); cell 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).
Supporting information
10.1107/S1600536812010574/hg5184sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: 10.1107/S1600536812010574/hg5184Isup2.cdx
Structure factors: contains datablock I. DOI: 10.1107/S1600536812010574/hg5184Isup3.hkl
Supporting information file. DOI: 10.1107/S1600536812010574/hg5184Isup4.cml
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).
Carbon-bound H atoms were placed in calculated positions (C—H 0.95 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2Ueq(C).Substituted
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 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 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
is shown in Figure 3.For pharmaceutical background to
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).Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).C15H9Cl2FO | F(000) = 600 |
Mr = 295.12 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/c | Melting point = 385–388 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.3390 (3) Å | Cell parameters from 9971 reflections |
b = 10.3896 (3) Å | θ = 2.7–28.3° |
c = 11.3930 (3) Å | µ = 0.49 mm−1 |
β = 97.078 (1)° | T = 200 K |
V = 1331.95 (6) Å3 | Block, colourless |
Z = 4 | 0.49 × 0.34 × 0.17 mm |
Bruker APEXII CCD diffractometer | 3329 independent reflections |
Radiation source: fine-focus sealed tube | 2742 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 28.4°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→15 |
Tmin = 0.798, Tmax = 0.920 | k = −13→13 |
23002 measured reflections | l = −15→15 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.040P)2 + 0.7737P] where P = (Fo2 + 2Fc2)/3 |
3329 reflections | (Δ/σ)max = 0.001 |
182 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
C15H9Cl2FO | V = 1331.95 (6) Å3 |
Mr = 295.12 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.3390 (3) Å | µ = 0.49 mm−1 |
b = 10.3896 (3) Å | T = 200 K |
c = 11.3930 (3) Å | 0.49 × 0.34 × 0.17 mm |
β = 97.078 (1)° |
Bruker APEXII CCD diffractometer | 3329 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2742 reflections with I > 2σ(I) |
Tmin = 0.798, Tmax = 0.920 | Rint = 0.025 |
23002 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.58 e Å−3 |
3329 reflections | Δρmin = −0.60 e Å−3 |
182 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | 0.83699 (6) | 0.03537 (6) | 0.06241 (5) | 0.06914 (19) | |
Cl2 | 0.43775 (5) | 0.32132 (6) | −0.01452 (5) | 0.07146 (19) | |
O1 | 0.67486 (13) | 0.20446 (13) | −0.16536 (10) | 0.0526 (3) | |
C1 | 0.76748 (14) | 0.40662 (15) | 0.08071 (14) | 0.0373 (3) | |
H1 | 0.7325 | 0.3570 | 0.1374 | 0.045* | |
C2 | 0.75116 (16) | 0.36328 (16) | −0.03056 (14) | 0.0410 (4) | |
H2 | 0.7832 | 0.4114 | −0.0901 | 0.049* | |
C3 | 0.68640 (16) | 0.24564 (16) | −0.06433 (13) | 0.0399 (3) | |
C11 | 0.83272 (14) | 0.52106 (15) | 0.12542 (14) | 0.0373 (3) | |
C12 | 0.89663 (17) | 0.59959 (17) | 0.05617 (17) | 0.0486 (4) | |
H12 | 0.8986 | 0.5798 | −0.0250 | 0.058* | |
C13 | 0.95691 (18) | 0.70569 (19) | 0.1055 (2) | 0.0569 (5) | |
H13 | 1.0018 | 0.7574 | 0.0584 | 0.068* | |
C14 | 0.9526 (2) | 0.7373 (2) | 0.2222 (2) | 0.0622 (6) | |
H14 | 0.9937 | 0.8112 | 0.2552 | 0.075* | |
C15 | 0.8889 (2) | 0.6619 (2) | 0.29125 (19) | 0.0602 (5) | |
H15 | 0.8850 | 0.6843 | 0.3715 | 0.072* | |
C16 | 0.83055 (16) | 0.55359 (17) | 0.24359 (15) | 0.0448 (4) | |
H16 | 0.7884 | 0.5007 | 0.2922 | 0.054* | |
C21 | 0.63217 (16) | 0.17125 (15) | 0.03024 (13) | 0.0407 (4) | |
C22 | 0.69437 (18) | 0.07128 (16) | 0.09046 (15) | 0.0467 (4) | |
C24 | 0.5310 (2) | 0.0283 (2) | 0.20019 (19) | 0.0693 (7) | |
H24 | 0.4966 | −0.0210 | 0.2574 | 0.083* | |
C26 | 0.51877 (18) | 0.19772 (19) | 0.05775 (16) | 0.0492 (4) | |
C23A | 0.6426 (2) | 0.00145 (19) | 0.17485 (17) | 0.0618 (6) | 0.747 (4) |
C25A | 0.4689 (2) | 0.1274 (3) | 0.14214 (19) | 0.0665 (7) | 0.747 (4) |
H25A | 0.3913 | 0.1478 | 0.1599 | 0.080* | 0.747 (4) |
F1A | 0.7017 (2) | −0.09064 (16) | 0.23597 (15) | 0.0758 (7) | 0.747 (4) |
C23B | 0.6426 (2) | 0.00145 (19) | 0.17485 (17) | 0.0618 (6) | 0.25 |
H23B | 0.6862 | −0.0665 | 0.2157 | 0.074* | 0.253 (4) |
C25B | 0.4689 (2) | 0.1274 (3) | 0.14214 (19) | 0.0665 (7) | 0.25 |
F2B | 0.3774 (5) | 0.1417 (8) | 0.1629 (6) | 0.099 (3) | 0.253 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0789 (4) | 0.0587 (3) | 0.0676 (3) | 0.0216 (3) | −0.0001 (3) | 0.0108 (2) |
Cl2 | 0.0627 (3) | 0.0829 (4) | 0.0700 (4) | 0.0201 (3) | 0.0129 (3) | 0.0075 (3) |
O1 | 0.0774 (9) | 0.0498 (7) | 0.0311 (6) | 0.0050 (6) | 0.0081 (6) | −0.0060 (5) |
C1 | 0.0450 (8) | 0.0320 (7) | 0.0358 (7) | 0.0024 (6) | 0.0077 (6) | 0.0041 (6) |
C2 | 0.0523 (9) | 0.0386 (8) | 0.0327 (7) | 0.0025 (7) | 0.0077 (6) | 0.0057 (6) |
C3 | 0.0512 (9) | 0.0373 (8) | 0.0311 (7) | 0.0084 (7) | 0.0051 (6) | 0.0000 (6) |
C11 | 0.0393 (8) | 0.0319 (7) | 0.0403 (8) | 0.0043 (6) | 0.0031 (6) | 0.0045 (6) |
C12 | 0.0544 (10) | 0.0406 (9) | 0.0516 (10) | 0.0008 (8) | 0.0098 (8) | 0.0096 (7) |
C13 | 0.0501 (10) | 0.0430 (9) | 0.0763 (14) | −0.0047 (8) | 0.0025 (9) | 0.0187 (9) |
C14 | 0.0637 (12) | 0.0423 (10) | 0.0743 (14) | −0.0108 (9) | −0.0161 (10) | 0.0041 (9) |
C15 | 0.0760 (14) | 0.0490 (11) | 0.0522 (11) | −0.0091 (10) | −0.0054 (10) | −0.0057 (9) |
C16 | 0.0537 (10) | 0.0392 (8) | 0.0409 (8) | −0.0021 (7) | 0.0027 (7) | 0.0004 (7) |
C21 | 0.0568 (10) | 0.0352 (8) | 0.0291 (7) | −0.0053 (7) | 0.0009 (6) | −0.0041 (6) |
C22 | 0.0665 (11) | 0.0360 (8) | 0.0354 (8) | −0.0068 (8) | −0.0030 (7) | −0.0018 (6) |
C24 | 0.0934 (17) | 0.0662 (14) | 0.0480 (11) | −0.0410 (13) | 0.0068 (11) | 0.0041 (10) |
C26 | 0.0567 (10) | 0.0520 (10) | 0.0385 (8) | −0.0074 (8) | 0.0036 (7) | −0.0054 (7) |
C23A | 0.0988 (18) | 0.0423 (10) | 0.0404 (10) | −0.0211 (10) | −0.0078 (10) | 0.0058 (8) |
C25A | 0.0706 (15) | 0.0780 (15) | 0.0518 (11) | −0.0294 (12) | 0.0114 (10) | −0.0063 (11) |
F1A | 0.1208 (17) | 0.0477 (9) | 0.0571 (10) | 0.0024 (9) | 0.0037 (10) | 0.0182 (7) |
C23B | 0.0988 (18) | 0.0423 (10) | 0.0404 (10) | −0.0211 (10) | −0.0078 (10) | 0.0058 (8) |
C25B | 0.0706 (15) | 0.0780 (15) | 0.0518 (11) | −0.0294 (12) | 0.0114 (10) | −0.0063 (11) |
F2B | 0.066 (4) | 0.136 (6) | 0.103 (5) | −0.033 (4) | 0.045 (3) | −0.012 (4) |
Cl1—C22 | 1.727 (2) | C14—C15 | 1.376 (3) |
Cl2—C26 | 1.728 (2) | C14—H14 | 0.9500 |
O1—C3 | 1.2198 (19) | C15—C16 | 1.382 (3) |
C1—C2 | 1.337 (2) | C15—H15 | 0.9500 |
C1—C11 | 1.459 (2) | C16—H16 | 0.9500 |
C1—H1 | 0.9500 | C21—C26 | 1.388 (3) |
C2—C3 | 1.453 (2) | C21—C22 | 1.388 (2) |
C2—H2 | 0.9500 | C22—C23A | 1.391 (3) |
C3—C21 | 1.516 (2) | C24—C23A | 1.362 (4) |
C11—C16 | 1.391 (2) | C24—C25A | 1.370 (4) |
C11—C12 | 1.398 (2) | C24—H24 | 0.9500 |
C12—C13 | 1.380 (3) | C26—C25A | 1.383 (3) |
C12—H12 | 0.9500 | C23A—F1A | 1.317 (3) |
C13—C14 | 1.377 (3) | C25A—H25A | 0.9500 |
C13—H13 | 0.9500 | ||
C2—C1—C11 | 127.65 (15) | C16—C15—H15 | 120.0 |
C2—C1—H1 | 116.2 | C15—C16—C11 | 120.87 (18) |
C11—C1—H1 | 116.2 | C15—C16—H16 | 119.6 |
C1—C2—C3 | 122.74 (15) | C11—C16—H16 | 119.6 |
C1—C2—H2 | 118.6 | C26—C21—C22 | 117.70 (16) |
C3—C2—H2 | 118.6 | C26—C21—C3 | 121.83 (15) |
O1—C3—C2 | 122.47 (16) | C22—C21—C3 | 120.45 (16) |
O1—C3—C21 | 119.07 (15) | C21—C22—C23A | 120.0 (2) |
C2—C3—C21 | 118.46 (13) | C21—C22—Cl1 | 120.01 (14) |
C16—C11—C12 | 118.46 (16) | C23A—C22—Cl1 | 119.97 (16) |
C16—C11—C1 | 117.86 (15) | C23A—C24—C25A | 119.2 (2) |
C12—C11—C1 | 123.68 (15) | C23A—C24—H24 | 120.4 |
C13—C12—C11 | 120.13 (18) | C25A—C24—H24 | 120.4 |
C13—C12—H12 | 119.9 | C25A—C26—C21 | 121.5 (2) |
C11—C12—H12 | 119.9 | C25A—C26—Cl2 | 119.02 (18) |
C14—C13—C12 | 120.62 (19) | C21—C26—Cl2 | 119.52 (14) |
C14—C13—H13 | 119.7 | F1A—C23A—C24 | 117.6 (2) |
C12—C13—H13 | 119.7 | F1A—C23A—C22 | 120.9 (2) |
C15—C14—C13 | 119.97 (19) | C24—C23A—C22 | 121.5 (2) |
C15—C14—H14 | 120.0 | C24—C25A—C26 | 120.2 (2) |
C13—C14—H14 | 120.0 | C24—C25A—H25A | 119.9 |
C14—C15—C16 | 119.9 (2) | C26—C25A—H25A | 119.9 |
C14—C15—H15 | 120.0 | ||
C11—C1—C2—C3 | 178.53 (15) | C26—C21—C22—C23A | 0.1 (2) |
C1—C2—C3—O1 | −177.72 (17) | C3—C21—C22—C23A | −178.32 (15) |
C1—C2—C3—C21 | 1.8 (2) | C26—C21—C22—Cl1 | −178.77 (13) |
C2—C1—C11—C16 | 175.07 (17) | C3—C21—C22—Cl1 | 2.8 (2) |
C2—C1—C11—C12 | −4.7 (3) | C22—C21—C26—C25A | 0.0 (3) |
C16—C11—C12—C13 | 0.8 (3) | C3—C21—C26—C25A | 178.42 (17) |
C1—C11—C12—C13 | −179.44 (16) | C22—C21—C26—Cl2 | 179.90 (12) |
C11—C12—C13—C14 | −1.6 (3) | C3—C21—C26—Cl2 | −1.7 (2) |
C12—C13—C14—C15 | 0.8 (3) | C25A—C24—C23A—F1A | 177.08 (19) |
C13—C14—C15—C16 | 0.8 (3) | C25A—C24—C23A—C22 | −0.8 (3) |
C14—C15—C16—C11 | −1.6 (3) | C21—C22—C23A—F1A | −177.52 (17) |
C12—C11—C16—C15 | 0.8 (3) | Cl1—C22—C23A—F1A | 1.4 (3) |
C1—C11—C16—C15 | −178.99 (17) | C21—C22—C23A—C24 | 0.3 (3) |
O1—C3—C21—C26 | −92.4 (2) | Cl1—C22—C23A—C24 | 179.16 (16) |
C2—C3—C21—C26 | 88.0 (2) | C23A—C24—C25A—C26 | 0.9 (3) |
O1—C3—C21—C22 | 85.9 (2) | C21—C26—C25A—C24 | −0.5 (3) |
C2—C3—C21—C22 | −93.60 (19) | Cl2—C26—C25A—C24 | 179.59 (16) |
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 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H9Cl2FO |
Mr | 295.12 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 200 |
a, b, c (Å) | 11.3390 (3), 10.3896 (3), 11.3930 (3) |
β (°) | 97.078 (1) |
V (Å3) | 1331.95 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.49 × 0.34 × 0.17 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.798, 0.920 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23002, 3329, 2742 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.111, 1.04 |
No. of reflections | 3329 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.58, −0.60 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O1i | 0.95 | 2.50 | 3.399 (2) | 157.9 |
C16—H16···O1i | 0.95 | 2.57 | 3.440 (2) | 153.0 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Acknowledgements
ASP thanks the University of Mysore for research facilities.
References
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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.