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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2641–o2642.
Published online 2009 October 3. doi:  10.1107/S1600536809037805
PMCID: PMC2971255

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

Abstract

The title compound, C15H10Cl2O, is a chalcone with 3-chloro­phenyl and 4-chloro­phenyl substituents bonded at the opposite ends of a propenone group, the biologically active region. The dihedral angle between mean planes of these two chloro-substituted benzene rings is 46.7 (7)° compared to 46.0 (1) and 32.4 (1)° in similar published sructures. The angles between the mean plane of the prop-2-en-1-one group and the mean planes of the 3-chloro­phenyl and 4-chloro­phenyl rings are 24.1 (2) and 29.63°, respectively. While no classical hydrogen bonds are present, weak inter­molecular C—H(...)π-ring inter­actions are observed, which contribute to the stability of crystal packing.

Related literature

For the potential use of chalcones or chalcone-rich plant extracts as drugs or food preservatives, see: Dhar (1981 [triangle]). For the biological and pharmaceutical activity of chalcones, see: Dimmock et al. (1999 [triangle]); Troeberg et al. (2000 [triangle]); Ram et al. (2000 [triangle]). For their applications as organic nonlinear optical materials, see: Sarojini et al. (2006 [triangle]). For the bis-(4-chloro­phen­yl) analog, see: Wang et al. (2005 [triangle]) and for the (2-chloro­phenyl, 4-chloro­phen­yl) analog, see: Fun et al. (2008b [triangle]). For antitumor and antioxidant activity studies and non-linear optical studies, see: Mukherjee et al. (2001 [triangle]); Poornesh et al. (2009 [triangle]); Shettigar et al. (2006 [triangle], 2008 [triangle]); Wang et al. (1997 [triangle]). For related structures, see: Butcher et al. (2007 [triangle]); Fischer et al. (2007 [triangle]); Fun et al. (2008a [triangle]); Harrison et al. (2006 [triangle]); Ng et al. (2006 [triangle]); Teh et al. (2007 [triangle]); Yathirajan et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2641-scheme1.jpg

Experimental

Crystal data

  • C15H10Cl2O
  • M r = 277.13
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2641-efi1.jpg
  • a = 5.8884 (9) Å
  • b = 7.3328 (9) Å
  • c = 14.6752 (16) Å
  • α = 102.821 (10)°
  • β = 95.003 (10)°
  • γ = 92.933 (11)°
  • V = 613.88 (14) Å3
  • Z = 2
  • Cu Kα radiation
  • μ = 4.61 mm−1
  • T = 110 K
  • 0.53 × 0.33 × 0.28 mm

Data collection

  • Oxford Diffraction Gemini R CCD diffractometer
  • Absorption correction: multi-scan (CrysAlisPro; Oxford Diffraction, 2007 [triangle]) T min = 0.067, T max = 0.275
  • 4041 measured reflections
  • 2402 independent reflections
  • 2147 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.133
  • S = 1.04
  • 2402 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.39 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/S1600536809037805/zs2009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037805/zs2009Isup2.hkl

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

Acknowledgments

KV thanks the UGC for the award of a Junior Research Fellowship and for an 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

Chalcones or 1,3-diaryl-2-propen-1-ones, belong to the flavonoid family. Chemically, they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α, β-unsaturated carbonyl system. A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone-rich plant extracts as drugs or food preservatives (Dhar, 1981). Among the many useful properties that chalcones have been reported to possess include anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic and anticancer activities (Dimmock et al., 1999). Many chalcones have been assessed for their high antimalarial activity, which is probably a result of Michael addition of nucleophilic species to the double bond of the enone (Troeberg et al., 2000; Ram et al., 2000). Chalcones are also finding applications as organic non-linear optical (NLO) materials due to their good SHG conversion efficiencies (Sarojini et al., 2006). Owing to the importance of these flavanoid analogs, the title chalcone (I), C15H10Cl2O has been synthesized and its crystal structure is reported here.

The title compound is a chalcone with 3-chlorophenyl and 4-chlorophenyl rings bonded at the opposite ends of a propenone group which is the biologically active region. The dihedral angle between mean planes of these two chloro-substituted benzene rings is 46.7 (7)° compared to 46.0 (1)° in the bis-(4-chlorophenyl) analog (Wang et al., 2005) and 32.4 (1)° in the (2-chlorophenyl, 4-chlorophenyl) analog (Fun et al., 2008b). The angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 3-chlorophenyl and 4-chlorophenyl rings are 24.1 (2)° and 29.63°, respectively. While no classical hydrogen bonds are present, weak intermolecular C–H···π-ring interactions are observed which contribute to the stability of crystal packing (Table 1).

Experimental

50% KOH was added to a mixture of 3-chloroacetophenone (0.01 mol) and p-chlorobenzaldehyde (0.01 mol) in 25 ml of ethanol. The mixture was stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol: yield 70% . Single crystals (m.p. 406–408 K) were grown from ethyl acetate by the slow evaporation method. Anal. found: C, 64.96; H, 3.61%; calc. for C15H10Cl2O: C 65.01; H, 3.64%.

Refinement

All of the H atoms were placed in their calculated positions and then refined using the riding model with C—H = 0.95 Å, and with Uiso(H) = 1.17–1.24Ueq(C).

Figures

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

Crystal data

C15H10Cl2OZ = 2
Mr = 277.13F(000) = 284
Triclinic, P1Dx = 1.499 Mg m3
Hall symbol: -P 1Melting point = 406–408 K
a = 5.8884 (9) ÅCu Kα radiation, λ = 1.54184 Å
b = 7.3328 (9) ÅCell parameters from 2900 reflections
c = 14.6752 (16) Åθ = 6.2–73.9°
α = 102.821 (10)°µ = 4.61 mm1
β = 95.003 (10)°T = 110 K
γ = 92.933 (11)°Block, colorless
V = 613.88 (14) Å30.53 × 0.33 × 0.28 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer2402 independent reflections
Radiation source: Enhance (Cu) X-ray Source2147 reflections with I > 2σ(I)
graphiteRint = 0.035
Detector resolution: 10.5081 pixels mm-1θmax = 73.9°, θmin = 6.2°
ω scansh = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)k = −4→9
Tmin = 0.067, Tmax = 0.275l = −18→18
4041 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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0992P)2 + 0.1931P] where P = (Fo2 + 2Fc2)/3
2402 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = −0.38 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
Cl10.57079 (8)−0.05763 (7)0.10784 (3)0.0235 (2)
Cl2−0.09011 (9)0.72931 (8)0.93921 (3)0.0286 (2)
O10.7088 (2)0.2250 (2)0.47821 (10)0.0233 (4)
C10.3892 (3)0.1004 (3)0.36950 (14)0.0161 (4)
C20.5165 (3)0.0748 (3)0.29158 (14)0.0154 (4)
H2A0.66960.12690.29800.019*
C30.4159 (3)−0.0275 (3)0.20525 (14)0.0164 (4)
C40.1936 (4)−0.1087 (3)0.19394 (15)0.0203 (4)
H4A0.1276−0.17900.13430.024*
C50.0704 (3)−0.0849 (3)0.27143 (15)0.0198 (4)
H5A−0.0810−0.14090.26490.024*
C60.1652 (3)0.0201 (3)0.35873 (14)0.0179 (4)
H6A0.07770.03710.41100.021*
C70.5008 (3)0.2095 (3)0.46235 (14)0.0177 (4)
C80.3516 (3)0.2980 (3)0.53315 (14)0.0191 (4)
H8A0.19590.31000.51390.023*
C90.4301 (3)0.3613 (3)0.62341 (14)0.0169 (4)
H9A0.58570.34390.64030.020*
C100.3008 (3)0.4551 (3)0.69935 (14)0.0161 (4)
C110.3922 (3)0.4779 (3)0.79294 (14)0.0174 (4)
H11A0.53900.43570.80580.021*
C120.2738 (3)0.5603 (3)0.86707 (14)0.0202 (4)
H12A0.33650.57290.93020.024*
C130.0614 (4)0.6243 (3)0.84698 (14)0.0189 (4)
C14−0.0325 (3)0.6083 (3)0.75532 (14)0.0177 (4)
H14A−0.17650.65550.74300.021*
C150.0860 (3)0.5226 (3)0.68181 (14)0.0167 (4)
H15A0.02130.50940.61890.020*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0286 (3)0.0275 (3)0.0145 (3)0.0029 (2)0.0075 (2)0.0028 (2)
Cl20.0267 (3)0.0389 (4)0.0174 (3)0.0087 (2)0.0064 (2)−0.0026 (2)
O10.0188 (7)0.0308 (9)0.0191 (7)0.0014 (6)0.0024 (6)0.0028 (6)
C10.0191 (9)0.0144 (9)0.0156 (10)0.0038 (7)0.0033 (7)0.0041 (7)
C20.0154 (9)0.0139 (9)0.0177 (10)0.0025 (7)0.0025 (7)0.0045 (7)
C30.0193 (10)0.0154 (9)0.0154 (9)0.0045 (7)0.0053 (7)0.0035 (7)
C40.0231 (10)0.0164 (10)0.0196 (10)0.0005 (8)−0.0013 (8)0.0017 (8)
C50.0162 (9)0.0168 (10)0.0264 (11)−0.0002 (8)0.0005 (8)0.0063 (8)
C60.0169 (9)0.0189 (10)0.0201 (10)0.0038 (8)0.0066 (7)0.0067 (8)
C70.0205 (10)0.0182 (10)0.0160 (10)0.0031 (8)0.0048 (7)0.0055 (8)
C80.0193 (10)0.0214 (10)0.0167 (10)0.0041 (8)0.0049 (7)0.0029 (8)
C90.0181 (9)0.0142 (9)0.0194 (10)0.0007 (7)0.0053 (7)0.0047 (8)
C100.0182 (10)0.0132 (9)0.0168 (10)−0.0016 (7)0.0038 (7)0.0031 (7)
C110.0183 (10)0.0147 (10)0.0183 (10)−0.0002 (7)0.0010 (7)0.0026 (7)
C120.0230 (10)0.0213 (10)0.0148 (9)0.0004 (8)0.0007 (7)0.0015 (8)
C130.0216 (10)0.0174 (10)0.0167 (10)−0.0002 (8)0.0067 (8)0.0006 (7)
C140.0169 (9)0.0150 (10)0.0211 (10)0.0006 (7)0.0033 (7)0.0036 (8)
C150.0194 (10)0.0162 (10)0.0142 (9)−0.0004 (8)0.0014 (7)0.0034 (7)

Geometric parameters (Å, °)

Cl1—C31.7414 (19)C8—C91.335 (3)
Cl2—C131.743 (2)C8—H8A0.9500
O1—C71.221 (2)C9—C101.469 (3)
C1—C61.398 (3)C9—H9A0.9500
C1—C21.405 (3)C10—C111.401 (3)
C1—C71.495 (3)C10—C151.405 (3)
C2—C31.386 (3)C11—C121.385 (3)
C2—H2A0.9500C11—H11A0.9500
C3—C41.391 (3)C12—C131.389 (3)
C4—C51.385 (3)C12—H12A0.9500
C4—H4A0.9500C13—C141.386 (3)
C5—C61.393 (3)C14—C151.386 (3)
C5—H5A0.9500C14—H14A0.9500
C6—H6A0.9500C15—H15A0.9500
C7—C81.480 (3)
C6—C1—C2119.42 (18)C7—C8—H8A119.1
C6—C1—C7122.00 (17)C8—C9—C10126.68 (19)
C2—C1—C7118.57 (17)C8—C9—H9A116.7
C3—C2—C1119.19 (17)C10—C9—H9A116.7
C3—C2—H2A120.4C11—C10—C15118.27 (19)
C1—C2—H2A120.4C11—C10—C9119.40 (18)
C2—C3—C4121.81 (18)C15—C10—C9122.33 (18)
C2—C3—Cl1119.60 (15)C12—C11—C10121.58 (19)
C4—C3—Cl1118.59 (16)C12—C11—H11A119.2
C5—C4—C3118.61 (19)C10—C11—H11A119.2
C5—C4—H4A120.7C11—C12—C13118.49 (19)
C3—C4—H4A120.7C11—C12—H12A120.8
C4—C5—C6120.93 (18)C13—C12—H12A120.8
C4—C5—H5A119.5C14—C13—C12121.62 (19)
C6—C5—H5A119.5C14—C13—Cl2119.12 (16)
C5—C6—C1120.02 (18)C12—C13—Cl2119.25 (16)
C5—C6—H6A120.0C15—C14—C13119.30 (19)
C1—C6—H6A120.0C15—C14—H14A120.4
O1—C7—C8121.66 (19)C13—C14—H14A120.4
O1—C7—C1120.42 (18)C14—C15—C10120.71 (18)
C8—C7—C1117.93 (17)C14—C15—H15A119.6
C9—C8—C7121.72 (19)C10—C15—H15A119.6
C9—C8—H8A119.1
C6—C1—C2—C31.0 (3)C1—C7—C8—C9164.85 (19)
C7—C1—C2—C3179.45 (17)C7—C8—C9—C10178.46 (18)
C1—C2—C3—C4−1.3 (3)C8—C9—C10—C11166.7 (2)
C1—C2—C3—Cl1179.19 (14)C8—C9—C10—C15−12.9 (3)
C2—C3—C4—C50.4 (3)C15—C10—C11—C121.6 (3)
Cl1—C3—C4—C5179.94 (15)C9—C10—C11—C12−178.04 (17)
C3—C4—C5—C60.8 (3)C10—C11—C12—C13−1.2 (3)
C4—C5—C6—C1−1.1 (3)C11—C12—C13—C14−0.4 (3)
C2—C1—C6—C50.2 (3)C11—C12—C13—Cl2−179.77 (15)
C7—C1—C6—C5−178.20 (18)C12—C13—C14—C151.4 (3)
C6—C1—C7—O1155.76 (19)Cl2—C13—C14—C15−179.14 (14)
C2—C1—C7—O1−22.7 (3)C13—C14—C15—C10−1.0 (3)
C6—C1—C7—C8−24.7 (3)C11—C10—C15—C14−0.4 (3)
C2—C1—C7—C8156.89 (18)C9—C10—C15—C14179.15 (17)
O1—C7—C8—C9−15.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2A···Cg2i0.952.983.608 (2)125
C5—H5A···Cg2ii0.952.883.488 (2)126
C14—H14A···Cg1iii0.952.773.474 (2)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: ZS2009).

References

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