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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o60.
Published online 2007 December 6. doi:  10.1107/S1600536807062010
PMCID: PMC2915018

(2E)-1-(4-Methyl­phen­yl)-3-(2,3,5-trichloro­phen­yl)prop-2-en-1-one

Abstract

In the title mol­ecule, C16H11Cl3O, the dihedral angle between the two benzene rings is 33.2 (1)°. The crystal packing is stabilized by C—H(...)O hydrogen bonds.

Related literature

For the uses of chalcones, see: John et al. (2007 [triangle]). For related crystal structures, see: Thiruvalluvar et al. (2007a [triangle],b [triangle]).

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Object name is e-64-00o60-scheme1.jpg

Experimental

Crystal data

  • C16H11Cl3O
  • M r = 325.60
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o60-efi3.jpg
  • a = 7.6432 (4) Å
  • b = 10.5118 (4) Å
  • c = 36.2356 (12) Å
  • V = 2911.3 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.62 mm−1
  • T = 200 (2) K
  • 0.34 × 0.27 × 0.22 mm

Data collection

  • Oxford Diffraction Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 [triangle]) T min = 0.818, T max = 0.877
  • 38087 measured reflections
  • 5035 independent reflections
  • 2561 reflections with I > 2σ(I)
  • R int = 0.069

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.168
  • S = 1.03
  • 5035 reflections
  • 181 parameters
  • H-atom parameters not refined
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062010/lx2037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062010/lx2037Isup2.hkl

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

Acknowledgments

RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer.

supplementary crystallographic information

Comment

Chalcones and their derivatives show some interesting physical properties like liquid crystalline nature and nonlinear optical effect(John et al., 2007). Thiruvalluvar et al. (2007a,b) have reported related crystal structures of chalcones. As a continuation of our work on chalcones, we report here the x-ray crystal structure of the title molecule, C16H11Cl3O, Fig.1.

The dihedral angle between the methylphenyl ring and the trichlorophenyl ring is 33.2 (1)°. The crystal packing is stabilized by C13—H13···Oi hydrogen bonds (Table 1 & Fig. 2; symmetry code as in Fig. 2)

Experimental

To the mixture of 2,3,5-trichlorobenzaldehyde (21 g, 0.1 mol) and 4-methylacetophenone (14.7 g, 0.11 mol) in methanol (100 ml), 20% of sodium hydroxide (8 g, 0.2 mol) was added at 288–293 K, after stirring for 8 h at 303 K. Solid obtained was filtered, washed with water and dried. The product was recrystallized using ethyl acetate. Yield was 27.6 g(85%).

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.96Å and Uiso = 1.2–1.5 times Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound with the atomic numbering and 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radius.
Fig. 2.
The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. [Symmetry code: (i) -x + 1/2, y - 1/2, z.]

Crystal data

C16H11Cl3ODx = 1.486 Mg m3
Mr = 325.60Melting point: 467(1) K
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8272 reflections
a = 7.6432 (4) Åθ = 4.7–32.4º
b = 10.5118 (4) ŵ = 0.62 mm1
c = 36.2356 (12) ÅT = 200 (2) K
V = 2911.3 (2) Å3Prism, colourless
Z = 80.34 × 0.27 × 0.22 mm
F000 = 1328

Data collection

Oxford Diffraction Gemini diffractometer5035 independent reflections
Radiation source: fine-focus sealed tube2561 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.069
Detector resolution: 10.5081 pixels mm-1θmax = 32.5º
T = 200(2) Kθmin = 4.7º
[var phi] and ω scansh = −11→10
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)k = −15→15
Tmin = 0.818, Tmax = 0.877l = −54→51
38087 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters not refined
wR(F2) = 0.168  w = 1/[σ2(Fo2) + (0.0546P)2 + 3.6539P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5035 reflectionsΔρmax = 0.32 e Å3
181 parametersΔρmin = −0.39 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
Cl10.04881 (12)0.50228 (8)0.19318 (2)0.0482 (3)
Cl2−0.10841 (14)0.32270 (9)0.25375 (2)0.0598 (3)
Cl3−0.06450 (13)−0.07474 (8)0.16142 (2)0.0501 (3)
O0.2908 (3)0.52884 (19)0.06638 (5)0.0419 (7)
C10.1438 (4)0.3651 (3)−0.05988 (7)0.0315 (8)
C20.2542 (4)0.4610 (3)−0.04685 (8)0.0358 (9)
C30.2707 (4)0.4818 (3)−0.00924 (7)0.0357 (9)
C40.1813 (3)0.4086 (2)0.01640 (7)0.0265 (7)
C50.0720 (4)0.3127 (3)0.00328 (7)0.0320 (8)
C60.0552 (4)0.2926 (3)−0.03434 (7)0.0341 (8)
C70.1220 (4)0.3410 (3)−0.10050 (8)0.0448 (10)
C80.0644 (3)0.2917 (3)0.14942 (7)0.0294 (8)
C90.0205 (4)0.3419 (3)0.18411 (7)0.0326 (8)
C10−0.0503 (4)0.2623 (3)0.21107 (7)0.0380 (9)
C11−0.0769 (4)0.1338 (3)0.20478 (8)0.0392 (9)
C12−0.0301 (4)0.0868 (3)0.17038 (7)0.0366 (9)
C130.0398 (4)0.1617 (3)0.14318 (7)0.0328 (8)
C140.2066 (4)0.4357 (3)0.05641 (7)0.0299 (8)
C150.1296 (4)0.3471 (3)0.08389 (7)0.0350 (9)
C160.1330 (4)0.3734 (3)0.11973 (7)0.0321 (8)
H20.318060.51195−0.063790.0429*
H30.345250.54801−0.000810.0428*
H50.008850.260930.020160.0385*
H6−0.019960.22678−0.042800.0409*
H7A0.196200.26939−0.107910.0671*
H7B0.156160.41717−0.114330.0671*
H7C−0.000660.32072−0.105760.0671*
H11−0.125250.080110.223230.0470*
H130.071600.125300.120130.0393*
H150.076940.270260.075690.0420*
H160.184380.451940.126860.0385*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0641 (6)0.0425 (4)0.0379 (4)0.0013 (4)0.0016 (4)−0.0104 (3)
Cl20.0763 (7)0.0702 (6)0.0328 (4)−0.0083 (5)0.0172 (4)−0.0141 (4)
Cl30.0708 (6)0.0372 (4)0.0422 (4)−0.0073 (4)0.0041 (4)0.0009 (3)
O0.0503 (14)0.0385 (12)0.0370 (10)−0.0092 (10)−0.0045 (10)−0.0030 (9)
C10.0329 (15)0.0324 (14)0.0292 (13)0.0067 (12)0.0021 (11)−0.0019 (11)
C20.0360 (16)0.0353 (15)0.0361 (14)−0.0053 (13)0.0051 (13)0.0031 (12)
C30.0342 (16)0.0341 (15)0.0387 (15)−0.0083 (13)−0.0009 (13)0.0007 (12)
C40.0259 (13)0.0239 (13)0.0296 (12)0.0032 (11)−0.0010 (11)0.0021 (10)
C50.0340 (15)0.0293 (14)0.0328 (13)−0.0049 (12)0.0030 (12)0.0046 (11)
C60.0349 (16)0.0326 (14)0.0347 (14)−0.0054 (13)−0.0023 (12)−0.0026 (11)
C70.0472 (19)0.057 (2)0.0302 (14)0.0024 (17)0.0017 (14)−0.0040 (14)
C80.0274 (14)0.0352 (14)0.0255 (12)0.0041 (12)−0.0020 (11)−0.0007 (10)
C90.0338 (15)0.0332 (14)0.0309 (13)0.0025 (12)−0.0027 (12)−0.0054 (11)
C100.0411 (17)0.0489 (18)0.0241 (12)−0.0014 (15)0.0030 (12)−0.0066 (12)
C110.0407 (17)0.0488 (18)0.0280 (14)−0.0054 (15)0.0003 (12)0.0007 (12)
C120.0435 (18)0.0376 (16)0.0286 (13)−0.0007 (14)−0.0025 (12)−0.0012 (11)
C130.0360 (15)0.0373 (15)0.0250 (12)0.0038 (13)−0.0008 (12)−0.0007 (11)
C140.0287 (14)0.0282 (14)0.0329 (13)0.0030 (12)−0.0029 (11)−0.0006 (11)
C150.0437 (17)0.0291 (14)0.0323 (14)−0.0019 (13)−0.0021 (13)−0.0014 (11)
C160.0333 (15)0.0316 (14)0.0314 (14)0.0022 (12)−0.0006 (12)−0.0022 (11)

Geometric parameters (Å, °)

Cl1—C91.731 (3)C10—C111.385 (4)
Cl2—C101.730 (3)C11—C121.388 (4)
Cl3—C121.749 (3)C12—C131.370 (4)
O—C141.226 (4)C14—C151.485 (4)
C1—C21.397 (4)C15—C161.328 (4)
C1—C61.377 (4)C2—H20.9500
C1—C71.503 (4)C3—H30.9500
C2—C31.386 (4)C5—H50.9500
C3—C41.386 (4)C6—H60.9500
C4—C51.393 (4)C7—H7A0.9800
C4—C141.490 (4)C7—H7B0.9800
C5—C61.385 (4)C7—H7C0.9800
C8—C91.404 (4)C11—H110.9500
C8—C131.398 (4)C13—H130.9500
C8—C161.473 (4)C15—H150.9500
C9—C101.396 (4)C16—H160.9500
Cl1···Cl23.1344 (12)C6···H3x2.9400
Cl2···C9i3.627 (3)C13···H7Axi3.0100
Cl2···Cl13.1344 (12)C13···H152.7100
Cl2···Cl3ii3.5154 (11)C14···H6viii2.7400
Cl3···Cl2iii3.5154 (11)C15···H52.6500
Cl3···C7iv3.592 (3)C15···H132.7100
Cl1···H162.6700H2···H7B2.4200
Cl3···H7Aiv2.9900H3···O2.4800
O···C13v3.372 (3)H3···C3vii2.9700
O···H32.4800H3···H3vii2.5700
O···H162.4700H3···C5v2.8600
O···H13v2.4300H3···C6v2.9400
O···H15v2.7500H5···C152.6500
C1···C14vi3.402 (4)H5···H152.0800
C3···C3vii3.589 (4)H6···H7C2.4900
C3···C5vi3.402 (4)H6···C4xi2.8600
C4···C5vi3.583 (4)H6···C14xi2.7400
C4···C4vi3.576 (3)H7A···C13viii3.0100
C5···C4vi3.583 (4)H7A···Cl3iv2.9900
C5···C3vi3.402 (4)H7B···H22.4200
C6···C14vi3.578 (4)H7C···H62.4900
C7···Cl3iv3.592 (3)H13···C152.7100
C7···C13viii3.548 (4)H13···H152.2200
C9···Cl2ix3.627 (3)H13···Ox2.4300
C13···Ox3.372 (3)H15···C52.6600
C13···C7xi3.548 (4)H15···C132.7100
C14···C6vi3.578 (4)H15···H52.0800
C14···C1vi3.402 (4)H15···H132.2200
C3···H3vii2.9700H15···Ox2.7500
C4···H6viii2.8600H16···Cl12.6700
C5···H152.6600H16···O2.4700
C5···H3x2.8600
C2—C1—C6118.0 (2)C4—C14—C15118.8 (2)
C2—C1—C7121.3 (3)C14—C15—C16121.2 (3)
C6—C1—C7120.7 (3)C8—C16—C15125.9 (3)
C1—C2—C3120.1 (3)C1—C2—H2120.00
C2—C3—C4121.8 (3)C3—C2—H2120.00
C3—C4—C5117.9 (2)C2—C3—H3119.00
C3—C4—C14118.8 (2)C4—C3—H3119.00
C5—C4—C14123.3 (2)C4—C5—H5120.00
C4—C5—C6120.1 (3)C6—C5—H5120.00
C1—C6—C5122.1 (3)C1—C6—H6119.00
C9—C8—C13118.7 (3)C5—C6—H6119.00
C9—C8—C16121.3 (3)C1—C7—H7A109.00
C13—C8—C16120.0 (2)C1—C7—H7B109.00
Cl1—C9—C8120.4 (2)C1—C7—H7C109.00
Cl1—C9—C10120.0 (2)H7A—C7—H7B109.00
C8—C9—C10119.6 (3)H7A—C7—H7C109.00
Cl2—C10—C9120.4 (2)H7B—C7—H7C109.00
Cl2—C10—C11117.9 (2)C10—C11—H11121.00
C9—C10—C11121.8 (3)C12—C11—H11121.00
C10—C11—C12117.2 (3)C8—C13—H13120.00
Cl3—C12—C11118.3 (2)C12—C13—H13120.00
Cl3—C12—C13118.9 (2)C14—C15—H15119.00
C11—C12—C13122.8 (3)C16—C15—H15119.00
C8—C13—C12119.9 (3)C8—C16—H16117.00
O—C14—C4120.5 (2)C15—C16—H16117.00
O—C14—C15120.8 (2)
C6—C1—C2—C3−0.7 (5)C9—C8—C13—C121.6 (4)
C7—C1—C2—C3179.5 (3)C16—C8—C13—C12−177.6 (3)
C2—C1—C6—C50.4 (5)C9—C8—C16—C15−158.6 (3)
C7—C1—C6—C5−179.8 (3)C13—C8—C16—C1520.6 (4)
C1—C2—C3—C40.7 (5)Cl1—C9—C10—Cl2−0.6 (4)
C2—C3—C4—C5−0.4 (4)Cl1—C9—C10—C11179.3 (2)
C2—C3—C4—C14179.5 (3)C8—C9—C10—Cl2−179.0 (2)
C3—C4—C5—C60.1 (4)C8—C9—C10—C110.8 (5)
C14—C4—C5—C6−179.8 (3)Cl2—C10—C11—C12179.8 (2)
C3—C4—C14—O7.2 (4)C9—C10—C11—C120.0 (5)
C3—C4—C14—C15−172.1 (3)C10—C11—C12—Cl3−179.3 (2)
C5—C4—C14—O−172.9 (3)C10—C11—C12—C130.0 (5)
C5—C4—C14—C157.8 (4)Cl3—C12—C13—C8178.4 (2)
C4—C5—C6—C1−0.1 (5)C11—C12—C13—C8−0.9 (5)
C13—C8—C9—Cl1179.9 (2)O—C14—C15—C167.5 (5)
C13—C8—C9—C10−1.6 (4)C4—C14—C15—C16−173.2 (3)
C16—C8—C9—Cl1−0.9 (4)C14—C15—C16—C8−178.6 (3)
C16—C8—C9—C10177.6 (3)

Symmetry codes: (i) x−1/2, y, −z+1/2; (ii) −x, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) −x, −y, −z; (v) −x+1/2, y+1/2, z; (vi) −x, −y+1, −z; (vii) −x+1, −y+1, −z; (viii) x+1/2, −y+1/2, −z; (ix) x+1/2, y, −z+1/2; (x) −x+1/2, y−1/2, z; (xi) x−1/2, −y+1/2, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···Ox0.952.433.372 (3)169

Symmetry codes: (x) −x+1/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2037).

References

  • Brandenburg, K. (1998). DIAMOND Version 2.1. Crystal Impact GbR, Bonn, Germany.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • John, A., Mithun, A., Holla, B. S., Shashikala, H. D., Umesh, G. & Chandrasekharan, K. (2007). Opt. Commun.296, 235–241.
  • Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED Versions 1.171.32. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.
  • Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473.
  • Sheldrick, G. M. (1997). SHELXL97 University of Göttingen, Germany. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Thiruvalluvar, A., Subramanyam, M., Butcher, R. J., Adhikari, A. V. & Karabasanagouda, T. (2007b). Acta Cryst. E63, o4716.
  • Thiruvalluvar, A., Subramanyam, M., Butcher, R. J., Adhikari, A. V. & Wagle, S. (2007a). Acta Cryst. E63, o4536.

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