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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o158.
Published online 2009 December 16. doi:  10.1107/S1600536809053446
PMCID: PMC2980037

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

Abstract

In the title compound, C15H10BrClO, the dihedral angle between mean planes of the bromo- and chloro-substituted benzene rings is 46.2 (2)° compared to 45.20 (9)° in the structure with the Cl substituent in the meta position of the aromatic ring. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-bromo­phenyl and 3-chloro­phenyl rings are 28.7 (5) and 24.2 (4)°, respectively. In the crystal, weak inter­molecular C—H(...)π inter­actions occur.

Related literature

For a related structure, see: Ng et al. (2006 [triangle]).

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Object name is e-66-0o158-scheme1.jpg

Experimental

Crystal data

  • C15H10BrClO
  • M r = 321.59
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o158-efi1.jpg
  • a = 5.9197 (8) Å
  • b = 7.3391 (11) Å
  • c = 14.8171 (17) Å
  • α = 101.929 (11)°
  • β = 94.371 (10)°
  • γ = 93.299 (11)°
  • V = 626.22 (15) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 6.29 mm−1
  • T = 110 K
  • 0.50 × 0.21 × 0.12 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector
  • Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.041, T max = 0.344
  • 3868 measured reflections
  • 2432 independent reflections
  • 2312 reflections with I > 2σ(I)
  • R int = 0.037

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.164
  • S = 1.07
  • 2432 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 1.78 e Å−3
  • Δρmin = −1.29 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97) (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053446/bt5130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053446/bt5130Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

KV thanksthe UGC for the sanction of a Junior Research Fellowship and for a SAP Chemical grant. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

In continuation of our interest in the synthesis and crystal structure determination of chalcones, the title chalcone, C15H10BrClO, is synthesized and its crystal structure is reported.

The title compound, (I), is a chalcone derivative with 4-bromophenyl and 3-chlorophenyl rings bonded at the opposite ends of a propenone group, the biologically active region (Fig.1). The dihedral angle between mean planes of the chloro and bromo substituted benzene rings is 46.2 (2)° compared to 45.20 (9)° (Ng et al. (2006)) and 46.70 (5)° for a similar related molecule. The angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 4-bromophenyl and 3-chlorophenyl rings are 28.7 (5)° and 24.2 (4)° and respectively. This compares to 20.66 (1)° and 24.54 (1)° in the similar structure. While no classical hydrogen bonds are present, weak intermolecular C–H···π-ring interactions are observed which contribute to the stability of crystal packing (Fig.2, Table 1).

Experimental

50% KOH was added to a mixture of 3-chloroacetophenone (0.01 mol) and p-bromobenzaldehyde (0.01 mol) in 25 ml of ethanol (Scheme 2). The mixture was stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from ethyl acetate by slow evaporation method with the yield of the compound being 70% (m.p.412–414 K). Analytical data for C15H10BrClO: Found (Calculated): C %: 55.97 (56.02); H%: 3.09 (3.13).

Refinement

All of the H atoms were placed in calculated positions and then refined using the riding model with C—H = 0.95 Å, and with Uiso(H) = 1.17–1.21Ueq(C).

Figures

Fig. 1.
Molecular structure of the title compound, C15H10BrClO, showing the atom labeling scheme and 50% probability displacement ellipsoids.
Fig. 2.
Packing diagram of the title compound, (I), viewed down the a axis.
Fig. 3.
The formation of the title compound.

Crystal data

C15H10BrClOZ = 2
Mr = 321.59F(000) = 320
Triclinic, P1Dx = 1.706 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54178 Å
a = 5.9197 (8) ÅCell parameters from 3370 reflections
b = 7.3391 (11) Åθ = 6.1–73.9°
c = 14.8171 (17) ŵ = 6.29 mm1
α = 101.929 (11)°T = 110 K
β = 94.371 (10)°Plate, colorless
γ = 93.299 (11)°0.50 × 0.21 × 0.12 mm
V = 626.22 (15) Å3

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector2432 independent reflections
Radiation source: fine-focus sealed tube2312 reflections with I > 2σ(I)
graphiteRint = 0.037
Detector resolution: 10.5081 pixels mm-1θmax = 74.0°, θmin = 6.1°
ω scansh = −7→6
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007)k = −9→8
Tmin = 0.041, Tmax = 0.344l = −18→18
3868 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1305P)2 + 0.5925P] where P = (Fo2 + 2Fc2)/3
2432 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 1.78 e Å3
0 restraintsΔρmin = −1.28 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br1A−0.10431 (6)0.72017 (5)0.94001 (2)0.0266 (2)
Cl1A0.58277 (16)−0.04318 (14)0.11075 (6)0.0269 (3)
O1A0.7080 (5)0.2207 (4)0.47588 (19)0.0270 (6)
C12A−0.0341 (6)0.5947 (5)0.7495 (3)0.0205 (7)
H12A−0.17770.64080.73780.025*
C1A0.3919 (6)0.1019 (5)0.3683 (3)0.0195 (7)
C2A0.5227 (6)0.0801 (5)0.2923 (3)0.0214 (7)
H2AA0.67560.13150.29920.026*
C11A0.0849 (6)0.5125 (5)0.6764 (3)0.0215 (7)
H11A0.02150.50190.61460.026*
C5A0.0776 (6)−0.0794 (5)0.2713 (3)0.0232 (8)
H5AA−0.0727−0.13640.26450.028*
C10A0.2967 (6)0.4452 (5)0.6929 (3)0.0207 (7)
C8A0.3490 (7)0.2931 (6)0.5299 (3)0.0245 (8)
H8AA0.19440.30440.51100.029*
C14A0.2701 (6)0.5451 (5)0.8595 (3)0.0229 (7)
H14A0.33180.55560.92160.027*
C3A0.4245 (6)−0.0180 (5)0.2068 (3)0.0200 (7)
C15A0.3894 (6)0.4648 (5)0.7854 (2)0.0210 (7)
H15A0.53520.42270.79740.025*
C13A0.0594 (7)0.6090 (5)0.8404 (2)0.0200 (7)
C6A0.1690 (6)0.0229 (5)0.3577 (3)0.0214 (7)
H6AA0.07990.03860.40910.026*
C7A0.5018 (6)0.2071 (5)0.4605 (2)0.0213 (7)
C9A0.4280 (6)0.3546 (5)0.6187 (3)0.0210 (7)
H9AA0.58260.33810.63510.025*
C4A0.2037 (6)−0.0988 (5)0.1951 (3)0.0228 (7)
H4AA0.1399−0.16610.13600.027*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br1A0.0240 (3)0.0339 (3)0.0202 (3)0.00673 (19)0.00381 (18)0.0001 (2)
Cl1A0.0292 (5)0.0316 (5)0.0200 (5)0.0051 (4)0.0061 (3)0.0036 (4)
O1A0.0217 (13)0.0343 (15)0.0224 (14)0.0029 (12)0.0001 (10)0.0010 (11)
C12A0.0183 (16)0.0213 (17)0.0211 (17)−0.0020 (13)−0.0003 (13)0.0044 (14)
C1A0.0205 (17)0.0196 (17)0.0191 (17)0.0030 (13)0.0014 (13)0.0057 (13)
C2A0.0207 (17)0.0211 (17)0.0213 (17)0.0032 (14)−0.0002 (13)0.0026 (14)
C11A0.0230 (17)0.0209 (17)0.0195 (17)−0.0015 (14)−0.0015 (13)0.0039 (13)
C5A0.0174 (16)0.0211 (17)0.030 (2)−0.0020 (13)−0.0039 (14)0.0061 (15)
C10A0.0222 (18)0.0199 (17)0.0194 (17)−0.0032 (14)−0.0003 (14)0.0050 (13)
C8A0.0228 (18)0.0278 (19)0.0217 (18)0.0016 (14)0.0005 (14)0.0033 (15)
C14A0.0227 (18)0.0233 (18)0.0213 (17)−0.0006 (14)−0.0019 (14)0.0036 (14)
C3A0.0201 (17)0.0211 (18)0.0197 (17)0.0058 (13)0.0029 (13)0.0047 (14)
C15A0.0179 (16)0.0258 (18)0.0192 (17)0.0022 (13)0.0018 (13)0.0045 (14)
C13A0.0252 (18)0.0181 (17)0.0155 (17)0.0027 (14)0.0045 (14)−0.0006 (13)
C6A0.0208 (17)0.0239 (18)0.0208 (18)0.0013 (14)0.0034 (13)0.0075 (14)
C7A0.0239 (17)0.0218 (17)0.0187 (17)0.0006 (14)0.0017 (14)0.0061 (14)
C9A0.0203 (17)0.0208 (17)0.0218 (18)−0.0003 (14)0.0008 (14)0.0055 (14)
C4A0.0240 (18)0.0218 (17)0.0203 (17)0.0035 (14)−0.0043 (14)0.0008 (14)

Geometric parameters (Å, °)

Br1A—C13A1.896 (4)C5A—H5AA0.9500
Cl1A—C3A1.747 (4)C10A—C15A1.413 (5)
O1A—C7A1.219 (5)C10A—C9A1.463 (5)
C12A—C11A1.388 (6)C8A—C9A1.339 (5)
C12A—C13A1.398 (5)C8A—C7A1.487 (5)
C12A—H12A0.9500C8A—H8AA0.9500
C1A—C6A1.395 (5)C14A—C13A1.387 (5)
C1A—C2A1.402 (5)C14A—C15A1.396 (5)
C1A—C7A1.503 (5)C14A—H14A0.9500
C2A—C3A1.387 (5)C3A—C4A1.387 (5)
C2A—H2AA0.9500C15A—H15A0.9500
C11A—C10A1.396 (5)C6A—H6AA0.9500
C11A—H11A0.9500C9A—H9AA0.9500
C5A—C4A1.388 (6)C4A—H4AA0.9500
C5A—C6A1.395 (5)
C11A—C12A—C13A119.4 (3)C15A—C14A—H14A120.7
C11A—C12A—H12A120.3C2A—C3A—C4A122.0 (3)
C13A—C12A—H12A120.3C2A—C3A—Cl1A119.4 (3)
C6A—C1A—C2A120.2 (3)C4A—C3A—Cl1A118.6 (3)
C6A—C1A—C7A121.8 (3)C14A—C15A—C10A121.1 (3)
C2A—C1A—C7A117.9 (3)C14A—C15A—H15A119.5
C3A—C2A—C1A118.7 (3)C10A—C15A—H15A119.5
C3A—C2A—H2AA120.7C14A—C13A—C12A121.5 (3)
C1A—C2A—H2AA120.7C14A—C13A—Br1A119.2 (3)
C12A—C11A—C10A120.8 (3)C12A—C13A—Br1A119.3 (3)
C12A—C11A—H11A119.6C1A—C6A—C5A119.6 (3)
C10A—C11A—H11A119.6C1A—C6A—H6AA120.2
C4A—C5A—C6A120.7 (3)C5A—C6A—H6AA120.2
C4A—C5A—H5AA119.6O1A—C7A—C8A122.6 (3)
C6A—C5A—H5AA119.6O1A—C7A—C1A120.2 (3)
C11A—C10A—C15A118.7 (4)C8A—C7A—C1A117.2 (3)
C11A—C10A—C9A123.1 (3)C8A—C9A—C10A125.6 (4)
C15A—C10A—C9A118.2 (3)C8A—C9A—H9AA117.2
C9A—C8A—C7A120.4 (4)C10A—C9A—H9AA117.2
C9A—C8A—H8AA119.8C3A—C4A—C5A118.8 (3)
C7A—C8A—H8AA119.8C3A—C4A—H4AA120.6
C13A—C14A—C15A118.5 (3)C5A—C4A—H4AA120.6
C13A—C14A—H14A120.7
C6A—C1A—C2A—C3A1.2 (5)C7A—C1A—C6A—C5A−177.6 (3)
C7A—C1A—C2A—C3A179.4 (3)C4A—C5A—C6A—C1A−1.9 (6)
C13A—C12A—C11A—C10A−0.4 (6)C9A—C8A—C7A—O1A−14.5 (6)
C12A—C11A—C10A—C15A−0.9 (6)C9A—C8A—C7A—C1A166.1 (4)
C12A—C11A—C10A—C9A179.0 (3)C6A—C1A—C7A—O1A155.6 (4)
C1A—C2A—C3A—C4A−1.7 (5)C2A—C1A—C7A—O1A−22.6 (5)
C1A—C2A—C3A—Cl1A178.8 (3)C6A—C1A—C7A—C8A−25.0 (5)
C13A—C14A—C15A—C10A−1.3 (6)C2A—C1A—C7A—C8A156.8 (3)
C11A—C10A—C15A—C14A1.7 (6)C7A—C8A—C9A—C10A178.5 (3)
C9A—C10A—C15A—C14A−178.1 (3)C11A—C10A—C9A—C8A−13.4 (6)
C15A—C14A—C13A—C12A0.0 (6)C15A—C10A—C9A—C8A166.4 (4)
C15A—C14A—C13A—Br1A−179.5 (3)C2A—C3A—C4A—C5A0.4 (5)
C11A—C12A—C13A—C14A0.8 (6)Cl1A—C3A—C4A—C5A179.8 (3)
C11A—C12A—C13A—Br1A−179.7 (3)C6A—C5A—C4A—C3A1.4 (6)
C2A—C1A—C6A—C5A0.6 (5)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1A–C6A ring and Cg2 is the centroid of the C10A–C15A ring.
D—H···AD—HH···AD···AD—H···A
C2A—H2AA···Cg2i0.952.973.588 (4)124
C5A—H5AA···Cg2ii0.952.843.463 (4)124
C12A—H12A···Cg1iii0.952.833.527 (4)131

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y, −z+1; (iii) −x, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5130).

References

  • Ng, S.-L., Razak, I. A., Fun, H.-K., Shettigar, V., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o2175–o2177.
  • Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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