Abstract
The molecule of the title compound, C15H9BrCl2O, is shown to be the E isomer, with the 3,4-dichlorobenzoyl and p-bromophenyl substituents in trans positions with respect to the chalcone olefin bond. The molecule is non-planar, the two aromatic rings forming a dihedral angle of 49.58 (1)°.
Related literature
For related literature on chalcones, see: Dhar (1981 ▶); Di Carlo et al. (1999 ▶); Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Sarojini et al. (2006 ▶). For related structures, see: Li et al. (2007 ▶, 2008 ▶); Wang et al. (2007 ▶); Tiang et al. (2007 ▶); Teh et al. (2006 ▶); Patil et al. (2006 ▶); Butcher et al. (2007 ▶).
Experimental
Crystal data
C15H9BrCl2O
M r = 356.05
Triclinic,
a = 5.9370 (5) Å
b = 7.7365 (6) Å
c = 14.8254 (11) Å
α = 81.347 (6)°
β = 88.182 (6)°
γ = 88.315 (6)°
V = 672.66 (9) Å3
Z = 2
Mo Kα radiation
μ = 3.44 mm−1
T = 293 K
0.30 × 0.24 × 0.18 mm
Data collection
Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.383, T max = 0.538
7411 measured reflections
3671 independent reflections
2762 reflections with I > 2σ(I)
R int = 0.024
Refinement
R[F 2 > 2σ(F 2)] = 0.048
wR(F 2) = 0.100
S = 1.14
3671 reflections
209 parameters
All H-atom parameters refined
Δρmax = 0.61 e Å−3
Δρmin = −0.50 e Å−3
Data collection: CrysAlis Pro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008162/ya2083sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008162/ya2083Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors are grateful to the Department of Science and Technology of the Government of India for funding under research project SR/S2/CMP-47/2003.
supplementary crystallographic information
Comment
1,3-Diaryl-2-propen-1-ones, also known as chalcones, belong to the flavonoid family. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the chalcone rich plant extracts as drugs or food preservatives (Dhar, 1981). Chalcones have also been reported to possess many useful properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Go et al., 2005). They are also finding application as organic nonlinear optical materials (Sarojini et al., 2006).
Owing to the general importance of these flavanoid analogues we report herein the synthesis and crystal structure of a new chalcone, (E)-3-(4-bromophenyl)-1-(3,4-dichlorophenyl)prop-2-en-1-one.
In the molecule of the title compound (Fig.1) the dichlorobenzoyl and p-bromophenyl substituents are in trans positions with respect to the C8=C9 double bond. The meolecule is non-planar; the dihedral angle formed by the aromatic rings C1-C6 and C10-C15 is equal to 49.58 (1)°.
Experimental
5 ml of 50% KOH was added to a mixture of 3,4-dichloroacetophenone (0.945 g, 0.005 mol) and 4-bromobenzaldehyde (0.92 g, 0.005 mol) in 25 ml of ethanol. The mixture was then stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol (m.p. 398-402 K; yield 74%). The single crystals were grown by slow evaporation from ethyl acetate. Analytical data: Found (Cald), %: C 50.58 (50.60); H 2.51 (2.55).
Refinement
All H atoms were located in the difference Fourier map and refined isotropically. The C—H distances are in the range of 0.90-0.96Å.
Figures
Fig. 1.
Molecular structure of the title compound; thermal displacement ellipsoids are drawn at the 50% probability level.
Crystal data
| C15H9BrCl2O | Z = 2 |
| Mr = 356.05 | F(000) = 352 |
| Triclinic, P1 | Dx = 1.758 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 5.9370 (5) Å | Cell parameters from 2762 reflections |
| b = 7.7365 (6) Å | θ = 3.2–30.3° |
| c = 14.8254 (11) Å | µ = 3.44 mm−1 |
| α = 81.347 (6)° | T = 293 K |
| β = 88.182 (6)° | Rectangular, pale yellow |
| γ = 88.315 (6)° | 0.30 × 0.24 × 0.18 mm |
| V = 672.66 (9) Å3 |
Data collection
| Oxford Diffraction Xcalibur diffractometer | 3671 independent reflections |
| Radiation source: fine-focus sealed tube | 2762 reflections with I > 2σ(I) |
| graphite | Rint = 0.024 |
| ω–2θ scans | θmax = 30.3°, θmin = 3.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −8→8 |
| Tmin = 0.383, Tmax = 0.538 | k = −10→10 |
| 7411 measured reflections | l = −20→20 |
Refinement
| Refinement on F2 | All H-atom parameters refined |
| Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0232P)2 + 0.974P] where P = (Fo2 + 2Fc2)/3 |
| R[F2 > 2σ(F2)] = 0.048 | (Δ/σ)max = 0.002 |
| wR(F2) = 0.100 | Δρmax = 0.61 e Å−3 |
| S = 1.14 | Δρmin = −0.50 e Å−3 |
| 3671 reflections | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 209 parameters | Extinction coefficient: 0.0163 (13) |
| 0 restraints |
Special details
| Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| H4 | −0.733 (6) | −0.335 (4) | 0.696 (2) | 0.029 (9)* | |
| H15 | −0.435 (6) | −0.108 (4) | 0.215 (2) | 0.032 (9)* | |
| H14 | −0.208 (6) | 0.023 (5) | 0.096 (2) | 0.038 (9)* | |
| H1 | −0.040 (6) | −0.628 (5) | 0.737 (2) | 0.039 (9)* | |
| H12 | 0.256 (6) | 0.100 (5) | 0.275 (2) | 0.044 (10)* | |
| H6 | −0.128 (6) | −0.465 (5) | 0.599 (3) | 0.047 (11)* | |
| H9 | −0.520 (6) | −0.192 (5) | 0.370 (2) | 0.041 (10)* | |
| H11 | 0.024 (6) | −0.027 (5) | 0.393 (3) | 0.041 (10)* | |
| H8 | −0.193 (6) | −0.212 (5) | 0.496 (2) | 0.045 (10)* | |
| Br1 | 0.22801 (7) | 0.18580 (5) | 0.07919 (2) | 0.04765 (14) | |
| Cl1 | −0.73344 (15) | −0.48572 (14) | 0.87746 (6) | 0.0488 (2) | |
| Cl2 | −0.26813 (16) | −0.68518 (13) | 0.90475 (6) | 0.0491 (2) | |
| C12 | 0.1124 (6) | 0.0635 (5) | 0.2638 (2) | 0.0365 (7) | |
| C13 | 0.0417 (5) | 0.0773 (4) | 0.1753 (2) | 0.0339 (7) | |
| C4 | −0.5964 (6) | −0.3937 (4) | 0.7036 (2) | 0.0325 (7) | |
| C3 | −0.5425 (5) | −0.4813 (4) | 0.7880 (2) | 0.0308 (6) | |
| C10 | −0.2309 (5) | −0.0822 (4) | 0.3167 (2) | 0.0314 (7) | |
| C6 | −0.2335 (6) | −0.4685 (5) | 0.6444 (2) | 0.0377 (8) | |
| C11 | −0.0236 (6) | −0.0170 (5) | 0.3342 (2) | 0.0354 (7) | |
| C5 | −0.4425 (5) | −0.3860 (4) | 0.6308 (2) | 0.0321 (7) | |
| C2 | −0.3345 (5) | −0.5675 (4) | 0.8006 (2) | 0.0316 (6) | |
| C9 | −0.3824 (6) | −0.1641 (5) | 0.3887 (2) | 0.0358 (7) | |
| C15 | −0.2963 (6) | −0.0639 (5) | 0.2264 (2) | 0.0350 (7) | |
| O1 | −0.7120 (4) | −0.2757 (4) | 0.52258 (17) | 0.0547 (7) | |
| C1 | −0.1805 (6) | −0.5621 (5) | 0.7283 (2) | 0.0385 (8) | |
| C7 | −0.5123 (6) | −0.2916 (5) | 0.5405 (2) | 0.0374 (7) | |
| C14 | −0.1609 (6) | 0.0134 (5) | 0.1552 (2) | 0.0375 (8) | |
| C8 | −0.3364 (6) | −0.2186 (5) | 0.4749 (2) | 0.0392 (8) |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.0529 (2) | 0.0481 (2) | 0.0392 (2) | −0.00965 (17) | 0.01013 (15) | 0.00191 (15) |
| Cl1 | 0.0466 (5) | 0.0615 (6) | 0.0345 (4) | 0.0011 (4) | 0.0124 (3) | 0.0022 (4) |
| Cl2 | 0.0572 (5) | 0.0459 (5) | 0.0403 (5) | 0.0040 (4) | −0.0066 (4) | 0.0064 (4) |
| C12 | 0.0330 (17) | 0.0381 (19) | 0.0386 (17) | −0.0066 (15) | −0.0010 (13) | −0.0049 (14) |
| C13 | 0.0387 (17) | 0.0287 (17) | 0.0320 (15) | 0.0015 (14) | 0.0051 (13) | 0.0008 (12) |
| C4 | 0.0310 (16) | 0.0332 (18) | 0.0330 (16) | −0.0052 (14) | 0.0002 (12) | −0.0027 (13) |
| C3 | 0.0339 (15) | 0.0287 (16) | 0.0297 (15) | −0.0068 (13) | 0.0047 (12) | −0.0038 (12) |
| C10 | 0.0366 (16) | 0.0291 (17) | 0.0284 (15) | −0.0029 (13) | −0.0002 (12) | −0.0039 (12) |
| C6 | 0.0348 (17) | 0.048 (2) | 0.0325 (16) | −0.0062 (15) | 0.0045 (13) | −0.0113 (14) |
| C11 | 0.0384 (17) | 0.0394 (19) | 0.0281 (15) | −0.0022 (15) | −0.0038 (13) | −0.0037 (13) |
| C5 | 0.0327 (15) | 0.0360 (18) | 0.0282 (15) | −0.0085 (14) | 0.0007 (12) | −0.0052 (13) |
| C2 | 0.0393 (17) | 0.0258 (16) | 0.0303 (15) | −0.0007 (13) | −0.0054 (12) | −0.0055 (12) |
| C9 | 0.0367 (17) | 0.0372 (19) | 0.0332 (16) | −0.0062 (15) | −0.0016 (13) | −0.0034 (13) |
| C15 | 0.0344 (17) | 0.0365 (19) | 0.0343 (16) | −0.0055 (14) | −0.0047 (13) | −0.0040 (14) |
| O1 | 0.0375 (13) | 0.085 (2) | 0.0372 (13) | −0.0068 (14) | −0.0018 (10) | 0.0060 (13) |
| C1 | 0.0371 (18) | 0.039 (2) | 0.0410 (18) | 0.0011 (15) | −0.0018 (14) | −0.0100 (15) |
| C7 | 0.0401 (18) | 0.042 (2) | 0.0299 (16) | −0.0066 (15) | 0.0000 (13) | −0.0042 (14) |
| C14 | 0.0461 (19) | 0.040 (2) | 0.0259 (15) | −0.0029 (16) | −0.0044 (13) | −0.0016 (13) |
| C8 | 0.0358 (17) | 0.048 (2) | 0.0328 (16) | −0.0096 (16) | −0.0014 (13) | −0.0006 (14) |
Geometric parameters (Å, °)
| Br1—C13 | 1.885 (3) | C6—C5 | 1.385 (5) |
| Cl1—C3 | 1.714 (3) | C6—H6 | 0.90 (4) |
| Cl2—C2 | 1.722 (3) | C11—H11 | 0.92 (4) |
| C12—C13 | 1.379 (5) | C5—C7 | 1.491 (4) |
| C12—C11 | 1.381 (4) | C2—C1 | 1.382 (5) |
| C12—H12 | 0.93 (4) | C9—C8 | 1.319 (5) |
| C13—C14 | 1.372 (5) | C9—H9 | 0.91 (4) |
| C4—C3 | 1.373 (4) | C15—C14 | 1.379 (4) |
| C4—C5 | 1.387 (4) | C15—H15 | 0.93 (3) |
| C4—H4 | 0.92 (3) | O1—C7 | 1.222 (4) |
| C3—C2 | 1.391 (4) | C1—H1 | 0.96 (4) |
| C10—C11 | 1.390 (5) | C7—C8 | 1.470 (4) |
| C10—C15 | 1.392 (4) | C14—H14 | 0.92 (4) |
| C10—C9 | 1.455 (4) | C8—H8 | 0.92 (4) |
| C6—C1 | 1.383 (5) | ||
| C13—C12—C11 | 119.3 (3) | C4—C5—C7 | 118.1 (3) |
| C13—C12—H12 | 119 (2) | C1—C2—C3 | 119.9 (3) |
| C11—C12—H12 | 121 (2) | C1—C2—Cl2 | 119.4 (3) |
| C14—C13—C12 | 121.6 (3) | C3—C2—Cl2 | 120.7 (2) |
| C14—C13—Br1 | 119.0 (2) | C8—C9—C10 | 127.7 (3) |
| C12—C13—Br1 | 119.3 (2) | C8—C9—H9 | 116 (2) |
| C3—C4—C5 | 120.6 (3) | C10—C9—H9 | 116 (2) |
| C3—C4—H4 | 120 (2) | C14—C15—C10 | 122.0 (3) |
| C5—C4—H4 | 120 (2) | C14—C15—H15 | 121 (2) |
| C4—C3—C2 | 120.0 (3) | C10—C15—H15 | 117 (2) |
| C4—C3—Cl1 | 119.8 (2) | C2—C1—C6 | 119.6 (3) |
| C2—C3—Cl1 | 120.2 (2) | C2—C1—H1 | 119 (2) |
| C11—C10—C15 | 117.9 (3) | C6—C1—H1 | 121 (2) |
| C11—C10—C9 | 122.8 (3) | O1—C7—C8 | 121.5 (3) |
| C15—C10—C9 | 119.3 (3) | O1—C7—C5 | 120.0 (3) |
| C1—C6—C5 | 120.8 (3) | C8—C7—C5 | 118.5 (3) |
| C1—C6—H6 | 117 (2) | C13—C14—C15 | 118.3 (3) |
| C5—C6—H6 | 122 (2) | C13—C14—H14 | 122 (2) |
| C12—C11—C10 | 120.8 (3) | C15—C14—H14 | 120 (2) |
| C12—C11—H11 | 119 (2) | C9—C8—C7 | 121.0 (3) |
| C10—C11—H11 | 120 (2) | C9—C8—H8 | 121 (2) |
| C6—C5—C4 | 119.1 (3) | C7—C8—H8 | 118 (2) |
| C6—C5—C7 | 122.9 (3) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2083).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008162/ya2083sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008162/ya2083Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report