Acta Cryst. (2008). E64, o1039 [ doi:10.1107/S1600536808013238 ]
In the title compound, C15H9Br2Cl2FO, the dihedral angle between the two aromatic rings is 6.0 (1)°. The dibromoethane fragment of the propan-1-one unit is disordered over two positions, with occupancies of ca 0.83 and 0.17. The crystal structure is stabilized by intermolecular C-H
O hydrogen bonds, C-H![[pi]](/logos/entities/pi_rmgif.gif)
interactions, and BrCl [3.505 (2) and 3.576 (6) Å] and ClF [3.176 (2) Å] short contacts.
1-(2,4-Dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one (1 mmol) was prepared by a literature procedure (Shivarama Holla et al., 2006). To a solution of 1-(2,4-dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one) (1 mmol) in chloroform (25 ml), bromine (1 mmol) was added slowly with stirring. After the completion of addition the reaction mixture was stirred for 24 h. Excess chloroform was distilled off and crude solid was filtered and dried. The precipitated compound was recrystallized from acetone.
The dibromoethane linkage is disordered over two positions with refined occupancies of 0.834 (6):0.166 (6). The C-Br distances were restrained to be equal, and Csp2-Csp3 and Csp3-Csp3 distances involving the disordered atoms were restrained to 1.50 (1) and 1.54 (1) Å, respectively. The Uij components of disordered atoms were restrained to approximate isotropic behaviour. H atoms were positioned geometrically [C—H = 0.95 or 1.00 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
![[Figure 1]](./ci2588fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. Only the major disorder component is shown. |
![[Figure 2]](./ci2588fig2thm.gif)
| Fig. 2. The crystal packing of the title compound, viewed along the a axis. Short intra- and intermolecular contacts and hydrogen bonds are shown as dashed lines. Only the major disorder component is shown. |
| C15H9Br2Cl2FO | F000 = 1760 |
| Mr = 454.94 | Dx = 1.957 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 4782 reflections |
| a = 7.1232 (1) Å | θ = 2.8–28.1º |
| b = 10.0757 (2) Å | µ = 5.60 mm−1 |
| c = 43.0262 (7) Å | T = 100 (2) K |
| V = 3088.04 (9) Å3 | Block, colourless |
| Z = 8 | 0.40 × 0.24 × 0.14 mm |
| Bruker SMART APEXII CCD area-detector diffractometer | 5857 independent reflections |
| Radiation source: fine-focus sealed tube | 3681 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.056 |
| T = 100(2) K | θmax = 33.2º |
| φ and ω scans | θmin = 1.0º |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −10→8 |
| Tmin = 0.211, Tmax = 0.508 | k = −15→15 |
| 26343 measured reflections | l = −52→66 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0309P)2 + 2.3603P] where P = (Fo2 + 2Fc2)/3 |
| S = 0.99 | (Δ/σ)max = 0.001 |
| 5857 reflections | Δρmax = 0.77 e Å−3 |
| 227 parameters | Δρmin = −0.76 e Å−3 |
| 60 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C15H9Br2Cl2FO | V = 3088.04 (9) Å3 |
| Mr = 454.94 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα |
| a = 7.1232 (1) Å | µ = 5.60 mm−1 |
| b = 10.0757 (2) Å | T = 100 (2) K |
| c = 43.0262 (7) Å | 0.40 × 0.24 × 0.14 mm |
| Bruker SMART APEXII CCD area-detector diffractometer | 5857 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3681 reflections with I > 2σ(I) |
| Tmin = 0.211, Tmax = 0.508 | Rint = 0.056 |
| 26343 measured reflections |
| R[F2 > 2σ(F2)] = 0.041 | 60 restraints |
| wR(F2) = 0.089 | H-atom parameters constrained |
| S = 0.99 | Δρmax = 0.77 e Å−3 |
| 5857 reflections | Δρmin = −0.76 e Å−3 |
| 227 parameters |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low–temperature attachment. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Cl1 | 0.58123 (10) | 0.31692 (7) | −0.003788 (15) | 0.02739 (16) | |
| Cl2 | 0.62659 (10) | −0.10513 (7) | 0.070833 (16) | 0.02701 (16) | |
| F1 | 0.3512 (3) | 0.42768 (15) | 0.04559 (4) | 0.0314 (4) | |
| O1 | 0.3888 (3) | −0.05963 (18) | 0.12256 (4) | 0.0211 (4) | |
| C1 | 0.0038 (4) | 0.0604 (3) | 0.21381 (6) | 0.0229 (6) | |
| H1 | 0.0475 | −0.0286 | 0.2151 | 0.028* | |
| C2 | −0.0915 (4) | 0.1152 (3) | 0.23859 (6) | 0.0243 (6) | |
| H2 | −0.1147 | 0.0635 | 0.2567 | 0.029* | |
| C3 | −0.1533 (4) | 0.2449 (3) | 0.23723 (7) | 0.0273 (6) | |
| H3 | −0.2197 | 0.2822 | 0.2543 | 0.033* | |
| C4 | −0.1181 (4) | 0.3209 (3) | 0.21087 (7) | 0.0260 (6) | |
| H4 | −0.1581 | 0.4107 | 0.2100 | 0.031* | |
| C5 | −0.0250 (5) | 0.2651 (3) | 0.18597 (7) | 0.0290 (7) | |
| H5 | −0.0025 | 0.3166 | 0.1679 | 0.035* | |
| C6 | 0.0365 (4) | 0.1337 (3) | 0.18715 (6) | 0.0265 (6) | |
| C9 | 0.3635 (4) | 0.0567 (3) | 0.11688 (6) | 0.0189 (5) | |
| C10 | 0.4255 (4) | 0.1189 (2) | 0.08738 (6) | 0.0176 (5) | |
| C11 | 0.3646 (4) | 0.2472 (3) | 0.07982 (6) | 0.0222 (6) | |
| H11 | 0.2883 | 0.2949 | 0.0941 | 0.027* | |
| C12 | 0.4138 (4) | 0.3047 (3) | 0.05211 (6) | 0.0216 (6) | |
| C13 | 0.5258 (4) | 0.2405 (3) | 0.03074 (6) | 0.0196 (5) | |
| C14 | 0.5896 (4) | 0.1134 (3) | 0.03752 (6) | 0.0203 (5) | |
| H14 | 0.6673 | 0.0677 | 0.0231 | 0.024* | |
| C15 | 0.5397 (4) | 0.0535 (2) | 0.06529 (6) | 0.0185 (5) | |
| Br1 | 0.4779 (3) | 0.1813 (3) | 0.17334 (5) | 0.0279 (4) | 0.834 (6) |
| Br2 | −0.06956 (14) | 0.02708 (17) | 0.12693 (3) | 0.0296 (2) | 0.834 (6) |
| C7 | 0.1226 (5) | 0.0653 (3) | 0.15969 (7) | 0.0194 (8) | 0.834 (6) |
| H7 | 0.1772 | −0.0209 | 0.1668 | 0.023* | 0.834 (6) |
| C8 | 0.2737 (5) | 0.1420 (4) | 0.14272 (7) | 0.0190 (8) | 0.834 (6) |
| H8 | 0.2216 | 0.2261 | 0.1339 | 0.023* | 0.834 (6) |
| Br1A | −0.0440 (7) | 0.0638 (6) | 0.11951 (14) | 0.0265 (8) | 0.166 (6) |
| Br2A | 0.4743 (16) | 0.1862 (16) | 0.1704 (2) | 0.0222 (16) | 0.166 (6) |
| C7A | 0.2193 (14) | 0.0999 (16) | 0.1700 (3) | 0.028 (5) | 0.166 (6) |
| H7A | 0.2405 | 0.0025 | 0.1728 | 0.033* | 0.166 (6) |
| C8A | 0.2088 (11) | 0.1248 (14) | 0.1348 (3) | 0.015 (4) | 0.166 (6) |
| H8A | 0.2190 | 0.2225 | 0.1311 | 0.018* | 0.166 (6) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0264 (4) | 0.0359 (4) | 0.0198 (3) | 0.0014 (3) | 0.0055 (3) | 0.0042 (3) |
| Cl2 | 0.0290 (4) | 0.0221 (3) | 0.0300 (3) | 0.0083 (3) | 0.0061 (3) | −0.0018 (3) |
| F1 | 0.0442 (11) | 0.0200 (8) | 0.0302 (9) | 0.0078 (8) | 0.0112 (8) | 0.0069 (7) |
| O1 | 0.0246 (11) | 0.0173 (9) | 0.0214 (9) | 0.0019 (8) | −0.0011 (8) | −0.0018 (7) |
| C1 | 0.0237 (15) | 0.0222 (13) | 0.0229 (13) | −0.0004 (12) | 0.0020 (11) | 0.0000 (10) |
| C2 | 0.0224 (15) | 0.0293 (15) | 0.0212 (13) | −0.0056 (12) | 0.0026 (11) | 0.0010 (11) |
| C3 | 0.0224 (16) | 0.0323 (16) | 0.0271 (15) | −0.0049 (13) | 0.0061 (12) | −0.0067 (12) |
| C4 | 0.0217 (15) | 0.0226 (14) | 0.0338 (15) | 0.0022 (12) | 0.0043 (12) | −0.0038 (12) |
| C5 | 0.0381 (19) | 0.0219 (14) | 0.0270 (15) | 0.0049 (13) | 0.0102 (13) | 0.0045 (11) |
| C6 | 0.0322 (18) | 0.0248 (14) | 0.0226 (13) | 0.0052 (13) | 0.0082 (12) | 0.0013 (11) |
| C9 | 0.0190 (14) | 0.0173 (12) | 0.0203 (13) | −0.0010 (11) | 0.0019 (10) | −0.0016 (10) |
| C10 | 0.0183 (13) | 0.0148 (12) | 0.0198 (12) | −0.0012 (10) | 0.0021 (10) | −0.0022 (9) |
| C11 | 0.0250 (15) | 0.0176 (13) | 0.0239 (13) | 0.0009 (12) | 0.0051 (11) | −0.0021 (10) |
| C12 | 0.0237 (14) | 0.0165 (12) | 0.0245 (13) | −0.0004 (11) | 0.0011 (11) | 0.0019 (10) |
| C13 | 0.0182 (14) | 0.0249 (14) | 0.0158 (12) | −0.0051 (11) | 0.0010 (10) | −0.0012 (10) |
| C14 | 0.0171 (13) | 0.0245 (14) | 0.0192 (12) | 0.0008 (11) | 0.0025 (10) | −0.0054 (10) |
| C15 | 0.0144 (13) | 0.0165 (12) | 0.0244 (13) | −0.0008 (10) | −0.0013 (10) | −0.0034 (10) |
| Br1 | 0.0181 (5) | 0.0296 (5) | 0.0359 (9) | −0.0023 (4) | −0.0012 (5) | −0.0105 (7) |
| Br2 | 0.0212 (3) | 0.0379 (5) | 0.0296 (4) | −0.0013 (3) | −0.0041 (3) | −0.0111 (3) |
| C7 | 0.0208 (18) | 0.0182 (15) | 0.0191 (15) | 0.0007 (13) | −0.0027 (13) | −0.0016 (12) |
| C8 | 0.022 (2) | 0.0175 (16) | 0.0173 (17) | −0.0011 (15) | −0.0004 (15) | −0.0024 (12) |
| Br1A | 0.0242 (14) | 0.0302 (17) | 0.0252 (16) | −0.0071 (12) | −0.0074 (11) | 0.0019 (12) |
| Br2A | 0.030 (3) | 0.031 (3) | 0.0061 (13) | −0.008 (2) | 0.0041 (14) | −0.0099 (13) |
| C7A | 0.027 (8) | 0.021 (7) | 0.035 (8) | −0.010 (6) | −0.010 (6) | 0.006 (6) |
| C8A | 0.015 (7) | 0.014 (7) | 0.016 (7) | −0.005 (6) | −0.007 (5) | 0.003 (5) |
| Cl1—C13 | 1.719 (3) | C9—C8 | 1.544 (4) |
| Cl2—C15 | 1.731 (3) | C10—C11 | 1.402 (4) |
| F1—C12 | 1.346 (3) | C10—C15 | 1.414 (4) |
| O1—C9 | 1.211 (3) | C11—C12 | 1.371 (4) |
| C1—C2 | 1.380 (4) | C11—H11 | 0.95 |
| C1—C6 | 1.384 (4) | C12—C13 | 1.379 (4) |
| C1—H1 | 0.95 | C13—C14 | 1.390 (4) |
| C2—C3 | 1.380 (4) | C14—C15 | 1.385 (4) |
| C2—H2 | 0.95 | C14—H14 | 0.95 |
| C3—C4 | 1.391 (4) | Br1—C8 | 2.002 (4) |
| C3—H3 | 0.95 | Br2—C7 | 2.002 (3) |
| C4—C5 | 1.380 (4) | C7—C8 | 1.513 (4) |
| C4—H4 | 0.95 | C7—H7 | 1.00 |
| C5—C6 | 1.395 (4) | C8—H8 | 1.00 |
| C5—H5 | 0.95 | Br1A—C8A | 2.013 (8) |
| C6—C7 | 1.499 (4) | Br2A—C7A | 2.014 (8) |
| C6—C7A | 1.536 (9) | C7A—C8A | 1.535 (9) |
| C9—C10 | 1.483 (4) | C7A—H7A | 1.00 |
| C9—C8A | 1.509 (9) | C8A—H8A | 1.00 |
| C2—C1—C6 | 120.6 (3) | C12—C13—C14 | 118.8 (2) |
| C2—C1—H1 | 119.7 | C12—C13—Cl1 | 119.9 (2) |
| C6—C1—H1 | 119.7 | C14—C13—Cl1 | 121.3 (2) |
| C1—C2—C3 | 120.2 (3) | C15—C14—C13 | 119.9 (2) |
| C1—C2—H2 | 119.9 | C15—C14—H14 | 120.0 |
| C3—C2—H2 | 119.9 | C13—C14—H14 | 120.0 |
| C2—C3—C4 | 119.9 (3) | C14—C15—C10 | 121.6 (2) |
| C2—C3—H3 | 120.1 | C14—C15—Cl2 | 115.5 (2) |
| C4—C3—H3 | 120.1 | C10—C15—Cl2 | 122.9 (2) |
| C5—C4—C3 | 119.7 (3) | C6—C7—C8 | 115.9 (3) |
| C5—C4—H4 | 120.2 | C6—C7—Br2 | 111.3 (2) |
| C3—C4—H4 | 120.2 | C8—C7—Br2 | 104.2 (2) |
| C4—C5—C6 | 120.6 (3) | C6—C7—H7 | 108.4 |
| C4—C5—H5 | 119.7 | C8—C7—H7 | 108.4 |
| C6—C5—H5 | 119.7 | Br2—C7—H7 | 108.4 |
| C1—C6—C5 | 118.9 (3) | C7—C8—C9 | 110.9 (3) |
| C1—C6—C7 | 118.5 (3) | C7—C8—Br1 | 107.5 (2) |
| C5—C6—C7 | 122.4 (3) | C9—C8—Br1 | 106.5 (2) |
| C1—C6—C7A | 115.1 (6) | C7—C8—H8 | 110.6 |
| C5—C6—C7A | 117.3 (6) | C9—C8—H8 | 110.6 |
| O1—C9—C10 | 122.5 (2) | Br1—C8—H8 | 110.6 |
| O1—C9—C8A | 116.5 (6) | C8A—C7A—C6 | 113.4 (8) |
| C10—C9—C8A | 117.6 (6) | C8A—C7A—Br2A | 89.1 (7) |
| O1—C9—C8 | 117.1 (2) | C6—C7A—Br2A | 131.6 (9) |
| C10—C9—C8 | 120.3 (2) | C8A—C7A—H7A | 106.7 |
| C11—C10—C15 | 116.9 (2) | C6—C7A—H7A | 106.7 |
| C11—C10—C9 | 119.7 (2) | Br2A—C7A—H7A | 106.7 |
| C15—C10—C9 | 123.4 (2) | C9—C8A—C7A | 113.2 (8) |
| C12—C11—C10 | 120.8 (2) | C9—C8A—Br1A | 110.3 (6) |
| C12—C11—H11 | 119.6 | C7A—C8A—Br1A | 108.4 (8) |
| C10—C11—H11 | 119.6 | C9—C8A—H8A | 108.3 |
| F1—C12—C11 | 119.0 (2) | C7A—C8A—H8A | 108.3 |
| F1—C12—C13 | 119.0 (2) | Br1A—C8A—H8A | 108.3 |
| C11—C12—C13 | 122.0 (2) | ||
| C6—C1—C2—C3 | −0.9 (4) | C1—C6—C7—C8 | −137.6 (3) |
| C1—C2—C3—C4 | −0.5 (4) | C5—C6—C7—C8 | 47.5 (4) |
| C2—C3—C4—C5 | 1.3 (4) | C7A—C6—C7—C8 | −44.3 (10) |
| C3—C4—C5—C6 | −0.9 (5) | C1—C6—C7—Br2 | 103.6 (3) |
| C2—C1—C6—C5 | 1.4 (5) | C5—C6—C7—Br2 | −71.2 (4) |
| C2—C1—C6—C7 | −173.7 (3) | C7A—C6—C7—Br2 | −163.1 (11) |
| C2—C1—C6—C7A | 148.2 (6) | C6—C7—C8—C9 | 174.9 (3) |
| C4—C5—C6—C1 | −0.5 (5) | Br2—C7—C8—C9 | −62.5 (3) |
| C4—C5—C6—C7 | 174.4 (3) | C6—C7—C8—Br1 | 58.9 (3) |
| C4—C5—C6—C7A | −146.6 (6) | Br2—C7—C8—Br1 | −178.49 (17) |
| O1—C9—C10—C11 | 169.1 (3) | O1—C9—C8—C7 | −38.7 (4) |
| C8A—C9—C10—C11 | 10.9 (5) | C10—C9—C8—C7 | 145.0 (3) |
| C8—C9—C10—C11 | −14.8 (4) | C8A—C9—C8—C7 | 55.5 (16) |
| O1—C9—C10—C15 | −8.5 (4) | O1—C9—C8—Br1 | 77.9 (3) |
| C8A—C9—C10—C15 | −166.7 (4) | C10—C9—C8—Br1 | −98.3 (3) |
| C8—C9—C10—C15 | 167.6 (3) | C8A—C9—C8—Br1 | 172.1 (18) |
| C15—C10—C11—C12 | 0.4 (4) | C1—C6—C7A—C8A | 151.0 (9) |
| C9—C10—C11—C12 | −177.3 (3) | C5—C6—C7A—C8A | −61.6 (12) |
| C10—C11—C12—F1 | 179.5 (2) | C7—C6—C7A—C8A | 46.7 (9) |
| C10—C11—C12—C13 | −0.7 (4) | C1—C6—C7A—Br2A | −97.9 (12) |
| F1—C12—C13—C14 | −179.8 (2) | C5—C6—C7A—Br2A | 49.5 (13) |
| C11—C12—C13—C14 | 0.3 (4) | C7—C6—C7A—Br2A | 157.8 (19) |
| F1—C12—C13—Cl1 | −0.7 (4) | O1—C9—C8A—C7A | 49.1 (10) |
| C11—C12—C13—Cl1 | 179.4 (2) | C10—C9—C8A—C7A | −151.4 (8) |
| C12—C13—C14—C15 | 0.3 (4) | C8—C9—C8A—C7A | −48.3 (12) |
| Cl1—C13—C14—C15 | −178.8 (2) | O1—C9—C8A—Br1A | −72.6 (8) |
| C13—C14—C15—C10 | −0.5 (4) | C10—C9—C8A—Br1A | 86.9 (8) |
| C13—C14—C15—Cl2 | 179.5 (2) | C8—C9—C8A—Br1A | −170 (2) |
| C11—C10—C15—C14 | 0.2 (4) | C6—C7A—C8A—C9 | −163.6 (8) |
| C9—C10—C15—C14 | 177.8 (3) | Br2A—C7A—C8A—C9 | 60.7 (10) |
| C11—C10—C15—Cl2 | −179.9 (2) | C6—C7A—C8A—Br1A | −40.8 (13) |
| C9—C10—C15—Cl2 | −2.2 (4) | Br2A—C7A—C8A—Br1A | −176.6 (8) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C5—H5···O1i | 0.95 | 2.45 | 3.392 (4) | 170 |
| C8—H8···O1i | 1.00 | 2.35 | 3.336 (4) | 169 |
| C11—H11···O1i | 0.95 | 2.29 | 3.229 (3) | 170 |
| C3—H3···Cg1ii | 0.95 | 2.96 | 3.652 (3) | 131 |
| Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x−3/2, y, −z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C5—H5···O1i | 0.95 | 2.45 | 3.392 (4) | 170 |
| C8—H8···O1i | 1.00 | 2.35 | 3.336 (4) | 169 |
| C11—H11···O1i | 0.95 | 2.29 | 3.229 (3) | 170 |
| C3—H3···Cg1ii | 0.95 | 2.96 | 3.652 (3) | 131 |
| Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x−3/2, y, −z−1/2. |
HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. HKF and IAR also thank the Malaysian Government and Universiti Sains Malaysia for the FRGS grant No. 203/PFIZIK/671064. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. This work was also supported by the Department of Science and Technology (DST), Government of India, grant No. SR/S2/LOP-17/2006.
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Derivatives of chalcone exhibit nonlinear optical (NLO) properties (Agrinskaya et al., 1999; Patil et al., 2006; John Kiran et al., 2007). We report here the crystal structure of the title compound (Fig 1), which crystallizes in a centrosymmetric space group and this precludes the presence of second-order NLO properties.
Bond lengths and angles in the title molecule have normal values (Allen et al., 1987). The dihedral angle between the benzene rings is 6.0 (1)°. The dibromoethane fragment of the propan-1-one unit is diordered over two positions.
The crystal packing is (Fig.2) stabilized by intermolecular C—H···O and weak C—H···π interactions involving the C1–C6 benzene ring (centroid Cg1). In addition, Br2···Cl2(-1+x,y,z) [3.505 (2) Å], Br1A···Cl2(-1+x,y,z) [3.576 (6) Å] and Cl1···F1(1-x,1-y,-z) [3.176 (2) Å] short contacts are oberved in the crystal structure.