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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 4| April 2009| Page o836
doi:10.1107/S1600536809008162

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

Rajni Kant,a* Kamni,b B. Narayana,c K. Veenac and H. S. Yathirajand

aDepartment of Physics, University of Jammu, Jammu Tawi 180 006, India, bSchool of Applied Physics and Mathematics, Shri Mata Vaishno Devi University, Jammu 182 121, India, cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri 576 006, India
*Correspondence e-mail: rk_paper@rediffmail.com

(Received 11 December 2008; accepted 5 March 2009; online 25 March 2009)

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[Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: John Wiley.]); Di Carlo et al. (1999[Di Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Sci. 65, 337-353.]); Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.]); Go et al. (2005[Go, M. L., Wu, X. & Liu, X. L. (2005). Curr. Med. Chem. 12, 483-499.]); Sarojini et al. (2006[Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54-59.]). For related structures, see: Li et al. (2007[Li, T.-D., Tian, N.-N., Bi, S. & Wan, J. (2007). Acta Cryst. E63, o3063.], 2008[Li, H., Sarojini, B. K., Raj, C. G. D., Madhu, L. N. & Yathirajan, H. S. (2008). Acta Cryst. E64, o2238.]); Wang et al. (2007[Wang, C.-Y., Xia, P., Han, Z.-P., Shen, R.-M. & Cui, N. (2007). Acta Cryst. E63, o1238-o1239.]); Tiang et al. (2007[Tian, N.-N., Bi, S., Xu, L.-L. & Wan, J. (2007). Acta Cryst. E63, o3602.]); Teh et al. (2006[Teh, J. B.-J., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o4380-o4381.]); Patil et al. (2006[Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1710-o1712.]); Butcher et al. (2007[Butcher, R. J., Jasinski, J. P., Yathirajan, H. S., Narayana, B. & Mayekar, A. N. (2007). Acta Cryst. E63, o4253-o4254.]).

[Scheme 1]

Experimental

Crystal data

  • C15H9BrCl2O

  • Mr = 356.05

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.383, Tmax = 0.538

  • 7411 measured reflections

  • 3671 independent reflections

  • 2762 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 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[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis Pro; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008162/ya2083sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809008162/ya2083Isup2.hkl

checkCIF report


Comment top

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)°.

Related literature top

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 top

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 top

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.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound; thermal displacement ellipsoids are drawn at the 50% probability level.
(E)-3-(4-Bromophenyl)-1-(3,4-dichlorophenyl)prop-2-en-1-one top
Crystal data top
C15H9BrCl2OZ = 2
Mr = 356.05F(000) = 352
Triclinic, P1Dx = 1.758 Mg m−3
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 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 top
Oxford Diffraction Xcalibur
diffractometer		3671 independent reflections
Radiation source: fine-focus sealed tube2762 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
Refinement on F2All 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) = 0.100Δρmax = 0.61 e Å−3
S = 1.14Δρmin = −0.50 e Å−3
3671 reflectionsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
209 parametersExtinction coefficient: 0.0163 (13)
0 restraints
Crystal data top
C15H9BrCl2Oγ = 88.315 (6)°
Mr = 356.05V = 672.66 (9) Å3
Triclinic, P1Z = 2
a = 5.9370 (5) ÅMo Kα radiation
b = 7.7365 (6) ŵ = 3.44 mm−1
c = 14.8254 (11) ÅT = 293 K
α = 81.347 (6)°0.30 × 0.24 × 0.18 mm
β = 88.182 (6)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer		3671 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		2762 reflections with I > 2σ(I)
Tmin = 0.383, Tmax = 0.538Rint = 0.024
7411 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.100All H-atom parameters refined
S = 1.14Δρmax = 0.61 e Å−3
3671 reflectionsΔρmin = −0.50 e Å−3
209 parameters
Special details top

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) top
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) top
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, º) top
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)

Experimental details

Crystal data
Chemical formulaC15H9BrCl2O
Mr356.05
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.9370 (5), 7.7365 (6), 14.8254 (11)
α, β, γ (°)81.347 (6), 88.182 (6), 88.315 (6)
V (Å3)672.66 (9)
Z2
Radiation typeMo Kα
µ (mm−1)3.44
Crystal size (mm)0.30 × 0.24 × 0.18
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.383, 0.538
No. of measured, independent and
observed [I > 2σ(I)] reflections		7411, 3671, 2762
Rint0.024
(sin θ/λ)max (Å−1)0.710
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.100, 1.14
No. of reflections3671
No. of parameters209
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.61, −0.50

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Acknowledgements

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.

References

First citationButcher, R. J., Jasinski, J. P., Yathirajan, H. S., Narayana, B. & Mayekar, A. N. (2007). Acta Cryst. E63, o4253–o4254.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationDhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: John Wiley.  Google Scholar
 First citationDi Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Sci. 65, 337–353.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationDimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149.  Web of Science PubMed CAS Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationGo, M. L., Wu, X. & Liu, X. L. (2005). Curr. Med. Chem. 12, 483–499.  CrossRef CAS Google Scholar
 First citationLi, H., Sarojini, B. K., Raj, C. G. D., Madhu, L. N. & Yathirajan, H. S. (2008). Acta Cryst. E64, o2238.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationLi, T.-D., Tian, N.-N., Bi, S. & Wan, J. (2007). Acta Cryst. E63, o3063.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationOxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationPatil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1710–o1712.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006). J. Cryst. Growth, 295, 54–59.  Web of Science CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTeh, J. B.-J., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o4380–o4381.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationTian, N.-N., Bi, S., Xu, L.-L. & Wan, J. (2007). Acta Cryst. E63, o3602.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationWang, C.-Y., Xia, P., Han, Z.-P., Shen, R.-M. & Cui, N. (2007). Acta Cryst. E63, o1238–o1239.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 4| April 2009| Page o836
doi:10.1107/S1600536809008162
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