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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o836.
Published online 2009 March 25. doi:  10.1107/S1600536809008162
PMCID: PMC2968950

(E)-3-(4-Bromo­phen­yl)-1-(3,4-dichloro­phen­yl)prop-2-en-1-one

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 [triangle]); Di Carlo et al. (1999 [triangle]); Dimmock et al. (1999 [triangle]); Go et al. (2005 [triangle]); Sarojini et al. (2006 [triangle]). For related structures, see: Li et al. (2007 [triangle], 2008 [triangle]); Wang et al. (2007 [triangle]); Tiang et al. (2007 [triangle]); Teh et al. (2006 [triangle]); Patil et al. (2006 [triangle]); Butcher et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o836-scheme1.jpg

Experimental

Crystal data

  • C15H9BrCl2O
  • M r = 356.05
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o836-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CrysAlis Pro; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

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

C15H9BrCl2OZ = 2
Mr = 356.05F(000) = 352
Triclinic, P1Dx = 1.758 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.9370 (5) ÅCell parameters from 2762 reflections
b = 7.7365 (6) Åθ = 3.2–30.3°
c = 14.8254 (11) ŵ = 3.44 mm1
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 diffractometer3671 independent reflections
Radiation source: fine-focus sealed tube2762 reflections with I > 2σ(I)
graphiteRint = 0.024
ω–2θ scansθmax = 30.3°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −8→8
Tmin = 0.383, Tmax = 0.538k = −10→10
7411 measured reflectionsl = −20→20

Refinement

Refinement on F2All H-atom parameters refined
Least-squares matrix: fullw = 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) = 0.100Δρmax = 0.61 e Å3
S = 1.14Δρmin = −0.50 e Å3
3671 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
209 parametersExtinction 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)

xyzUiso*/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)*
H120.256 (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)*
H110.024 (6)−0.027 (5)0.393 (3)0.041 (10)*
H8−0.193 (6)−0.212 (5)0.496 (2)0.045 (10)*
Br10.22801 (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)
C120.1124 (6)0.0635 (5)0.2638 (2)0.0365 (7)
C130.0417 (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)

U11U22U33U12U13U23
Br10.0529 (2)0.0481 (2)0.0392 (2)−0.00965 (17)0.01013 (15)0.00191 (15)
Cl10.0466 (5)0.0615 (6)0.0345 (4)0.0011 (4)0.0124 (3)0.0022 (4)
Cl20.0572 (5)0.0459 (5)0.0403 (5)0.0040 (4)−0.0066 (4)0.0064 (4)
C120.0330 (17)0.0381 (19)0.0386 (17)−0.0066 (15)−0.0010 (13)−0.0049 (14)
C130.0387 (17)0.0287 (17)0.0320 (15)0.0015 (14)0.0051 (13)0.0008 (12)
C40.0310 (16)0.0332 (18)0.0330 (16)−0.0052 (14)0.0002 (12)−0.0027 (13)
C30.0339 (15)0.0287 (16)0.0297 (15)−0.0068 (13)0.0047 (12)−0.0038 (12)
C100.0366 (16)0.0291 (17)0.0284 (15)−0.0029 (13)−0.0002 (12)−0.0039 (12)
C60.0348 (17)0.048 (2)0.0325 (16)−0.0062 (15)0.0045 (13)−0.0113 (14)
C110.0384 (17)0.0394 (19)0.0281 (15)−0.0022 (15)−0.0038 (13)−0.0037 (13)
C50.0327 (15)0.0360 (18)0.0282 (15)−0.0085 (14)0.0007 (12)−0.0052 (13)
C20.0393 (17)0.0258 (16)0.0303 (15)−0.0007 (13)−0.0054 (12)−0.0055 (12)
C90.0367 (17)0.0372 (19)0.0332 (16)−0.0062 (15)−0.0016 (13)−0.0034 (13)
C150.0344 (17)0.0365 (19)0.0343 (16)−0.0055 (14)−0.0047 (13)−0.0040 (14)
O10.0375 (13)0.085 (2)0.0372 (13)−0.0068 (14)−0.0018 (10)0.0060 (13)
C10.0371 (18)0.039 (2)0.0410 (18)0.0011 (15)−0.0018 (14)−0.0100 (15)
C70.0401 (18)0.042 (2)0.0299 (16)−0.0066 (15)0.0000 (13)−0.0042 (14)
C140.0461 (19)0.040 (2)0.0259 (15)−0.0029 (16)−0.0044 (13)−0.0016 (13)
C80.0358 (17)0.048 (2)0.0328 (16)−0.0096 (16)−0.0014 (13)−0.0006 (14)

Geometric parameters (Å, °)

Br1—C131.885 (3)C6—C51.385 (5)
Cl1—C31.714 (3)C6—H60.90 (4)
Cl2—C21.722 (3)C11—H110.92 (4)
C12—C131.379 (5)C5—C71.491 (4)
C12—C111.381 (4)C2—C11.382 (5)
C12—H120.93 (4)C9—C81.319 (5)
C13—C141.372 (5)C9—H90.91 (4)
C4—C31.373 (4)C15—C141.379 (4)
C4—C51.387 (4)C15—H150.93 (3)
C4—H40.92 (3)O1—C71.222 (4)
C3—C21.391 (4)C1—H10.96 (4)
C10—C111.390 (5)C7—C81.470 (4)
C10—C151.392 (4)C14—H140.92 (4)
C10—C91.455 (4)C8—H80.92 (4)
C6—C11.383 (5)
C13—C12—C11119.3 (3)C4—C5—C7118.1 (3)
C13—C12—H12119 (2)C1—C2—C3119.9 (3)
C11—C12—H12121 (2)C1—C2—Cl2119.4 (3)
C14—C13—C12121.6 (3)C3—C2—Cl2120.7 (2)
C14—C13—Br1119.0 (2)C8—C9—C10127.7 (3)
C12—C13—Br1119.3 (2)C8—C9—H9116 (2)
C3—C4—C5120.6 (3)C10—C9—H9116 (2)
C3—C4—H4120 (2)C14—C15—C10122.0 (3)
C5—C4—H4120 (2)C14—C15—H15121 (2)
C4—C3—C2120.0 (3)C10—C15—H15117 (2)
C4—C3—Cl1119.8 (2)C2—C1—C6119.6 (3)
C2—C3—Cl1120.2 (2)C2—C1—H1119 (2)
C11—C10—C15117.9 (3)C6—C1—H1121 (2)
C11—C10—C9122.8 (3)O1—C7—C8121.5 (3)
C15—C10—C9119.3 (3)O1—C7—C5120.0 (3)
C1—C6—C5120.8 (3)C8—C7—C5118.5 (3)
C1—C6—H6117 (2)C13—C14—C15118.3 (3)
C5—C6—H6122 (2)C13—C14—H14122 (2)
C12—C11—C10120.8 (3)C15—C14—H14120 (2)
C12—C11—H11119 (2)C9—C8—C7121.0 (3)
C10—C11—H11120 (2)C9—C8—H8121 (2)
C6—C5—C4119.1 (3)C7—C8—H8118 (2)
C6—C5—C7122.9 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2083).

References

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Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography