Literature DB >> 21578256

(2E)-1-(3-Chloro-phen-yl)-3-(4-chloro-phen-yl)prop-2-en-1-one.

Jerry P Jasinski, Ray J Butcher, B Narayana, K Veena, H S Yathirajan.   

Abstract

The title compound, C(15)H(10)Cl(2)O, is a chalcone with 3-chloro-phenyl and 4-chloro-phenyl 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-chloro-phenyl and 4-chloro-phenyl rings are 24.1 (2) and 29.63°, respectively. While no classical hydrogen bonds are present, weak inter-molecular C-H⋯π-ring inter-actions are observed, which contribute to the stability of crystal packing.

Entities:  

Year:  2009        PMID： 21578256      PMCID： PMC2971255          DOI： 10.1107/S1600536809037805

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C15H10Cl2O M = 277.13 Triclinic, 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 ▶) 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 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. 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
C15H10Cl2OZ = 2
Mr = 277.13F(000) = 284
Triclinic, P1Dx = 1.499 Mg m−3
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 mm−1
β = 95.003 (10)°T = 110 K
γ = 92.933 (11)°Block, colorless
V = 613.88 (14) Å30.53 × 0.33 × 0.28 mm
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 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 Å−3
0 restraintsΔρmin = −0.38 e Å−3
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.
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*
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)
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)
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
Table 1

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) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring and Cg2 is the centroid of the C10–C15 ring.

  8 in total

Review 1.  Bioactivities of chalcones.

Authors:  J R Dimmock; D W Elias; M A Beazely; N M Kandepu
Journal:  Curr Med Chem       Date:  1999-12       Impact factor: 4.530

2.  Synthetic and biological activity evaluation studies on novel 1,3-diarylpropenones.

Authors:  S Mukherjee; V Kumar; A K Prasad; H G Raj; M E Bracke; C E Olsen; S C Jain; V S Parmar
Journal:  Bioorg Med Chem       Date:  2001-02       Impact factor: 3.641

3.  Oxygenated chalcones and bischalcones as potential antimalarial agents.

Authors:  V J Ram; A S Saxena; S Srivastava; S Chandra
Journal:  Bioorg Med Chem Lett       Date:  2000-10-02       Impact factor: 2.823

4.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

5.  Chalcone, acyl hydrazide, and related amides kill cultured Trypanosoma brucei brucei.

Authors:  L Troeberg; X Chen; T M Flaherty; R E Morty; M Cheng; H Hua; C Springer; J H McKerrow; G L Kenyon; J D Lonsdale-Eccles; T H Coetzer; F E Cohen
Journal:  Mol Med       Date:  2000-08       Impact factor: 6.354

6.  Investigation of the inhibitory effect of broussochalcone A on respiratory burst in neutrophils.

Authors:  J P Wang; L T Tsao; S L Raung; C N Lin
Journal:  Eur J Pharmacol       Date:  1997-02-12       Impact factor: 4.432

7.  (E)-3-(2-Chloro-phen-yl)-1-(4-chloro-phen-yl)prop-2-en-1-one.

Authors:  Hoong-Kun Fun; Samuel Robinson Jebas; Ibrahim Abdul Razak; P S Patil; S M Dharmaprakash; E Deepak D'Silva
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-30

8.  (E)-1-(4-Amino-phen-yl)-3-(2-chloro-phen-yl)prop-2-en-1-one.

Authors:  Hoong-Kun Fun; Reza Kia; P S Patil; S M Dharmaprakash; Ibrahim Abdul Razak
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-27
  8 in total
  1 in total

1.  (2E)-1-(2-Bromo-phen-yl)-3-(4-chloro-phen-yl)prop-2-en-1-one.

Authors:  Jerry P Jasinski; Ray J Butcher; K Veena; B Narayana; H S Yathirajan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-16
  1 in total

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