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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o936.
Published online 2008 April 30. doi:  10.1107/S1600536808011008
PMCID: PMC2961235

1-(2,4-Dichloro­phen­yl)-3-(4-methyl­phen­yl)prop-2-en-1-one

Abstract

The mol­ecule of the title compound, C16H12Cl2O, adopts an E configuration. The dihedral angle between the two benzene rings is 42.09 (5)°. In the crystal structure, mol­ecules are linked into a three-dimensional framework by weak C—H(...)O inter­actions and by C—H(...)π inter­actions involving the methyl­phenyl ring.

Related literature

For related literature, see: Agrinskaya et al. (1999 [triangle]); Gu et al. (2008 [triangle]); Patil et al. (2006 [triangle]); Patil, Dharmaprakash et al. (2007 [triangle]); Patil, Teh et al. (2007 [triangle]).

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Object name is e-64-0o936-scheme1.jpg

Experimental

Crystal data

  • C16H12Cl2O
  • M r = 291.16
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o936-efi1.jpg
  • a = 12.54850 (1) Å
  • b = 7.47750 (1) Å
  • c = 28.7764 (3) Å
  • V = 2700.13 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.47 mm−1
  • T = 100.0 (1) K
  • 0.47 × 0.39 × 0.20 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.811, T max = 0.914
  • 50054 measured reflections
  • 7296 independent reflections
  • 4995 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.148
  • S = 1.07
  • 7296 reflections
  • 173 parameters
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.53 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011008/ci2584sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011008/ci2584Isup2.hkl

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

Acknowledgments

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for the award of a post-doctoral research fellowship. PSP thanks the DRDO, Government of India, for a Senior Research Fellowship (SRF). This work is also supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006.

supplementary crystallographic information

Comment

Chalcone derivatives have been studied extensively owing to their fascinating, technologically relevant nonlinear optical properties (Gu et al., 2008; Agrinskaya et al., 1999; Patil et al., 2006; Patil, Dharmaprakash et al., 2007; Patil, Teh et al., 2007).

The title molecule exhibits an E configuration with respect to the C8═C9 double bond [1.3424 (14) Å]; the C7—C8—-C9—-C10 torsion angle is 179.61 (11)°. The dihedral angle between the two benzene rings is 42.09 (5)°. The bond lengths and angles in the title molecule have normal values.

The crystal structure is stabilized by weak C—H···O intermolecular hydrogen bonding interactions (Table 1), which link the molecules into a three-dimensional framework (Fig. 2). In addition weak C—H..π interactions involving the C10—C15 benzene ring (centroid Cg1) is observed.

Experimental

The title compound was synthesized by the condensation of p-tolualdehyde (0.01 mol) with 2,4-dichloroacetophenone (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 2 h, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was collected by filtration and dried. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of an acetone solution at room temperature.

Refinement

H atoms were positioned geometrically [C-H = 0.93 (aromatic) or 0.96 Å (methyl)] and refined using a riding model, with Uiso(H) = 1.5Ueq(methyl C) or 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
Fig. 2.
The crystal packing of the title compound, viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C16H12Cl2OF000 = 1200
Mr = 291.16Dx = 1.432 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9639 reflections
a = 12.54850 (1) Åθ = 2.8–34.6º
b = 7.47750 (1) ŵ = 0.47 mm1
c = 28.7764 (3) ÅT = 100.0 (1) K
V = 2700.13 (3) Å3Block, colourless
Z = 80.47 × 0.39 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer7296 independent reflections
Radiation source: fine-focus sealed tube4995 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.052
T = 100.0(1) Kθmax = 37.9º
[var phi] and ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −21→21
Tmin = 0.811, Tmax = 0.914k = −12→12
50054 measured reflectionsl = −48→49

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.148  w = 1/[σ2(Fo2) + (0.078P)2 + 0.0443P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
7296 reflectionsΔρmax = 0.64 e Å3
173 parametersΔρmin = −0.53 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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
Cl10.46470 (2)0.76088 (4)0.057148 (10)0.02125 (8)
Cl20.36980 (3)0.56187 (5)−0.116828 (9)0.02538 (9)
O10.13288 (7)0.72551 (12)0.08499 (3)0.02032 (17)
C10.37202 (9)0.67308 (15)0.01850 (4)0.0158 (2)
C20.40554 (10)0.64861 (15)−0.02709 (4)0.0177 (2)
H20.47590.6696−0.03560.021*
C30.33080 (10)0.59184 (15)−0.05947 (4)0.0177 (2)
C40.22518 (9)0.56292 (16)−0.04764 (4)0.0183 (2)
H40.17600.5265−0.06990.022*
C50.19470 (9)0.58948 (15)−0.00210 (4)0.0173 (2)
H50.12380.57150.00600.021*
C60.26690 (9)0.64245 (14)0.03220 (3)0.01531 (19)
C70.22310 (9)0.66606 (15)0.08060 (4)0.0165 (2)
C80.28861 (9)0.60913 (15)0.12039 (4)0.0168 (2)
H80.35120.54580.11510.020*
C90.25956 (10)0.64712 (15)0.16419 (4)0.0168 (2)
H90.19620.71000.16800.020*
C100.31720 (9)0.59981 (15)0.20655 (4)0.01556 (19)
C110.27256 (10)0.64353 (15)0.24970 (4)0.0179 (2)
H110.20750.70310.25080.021*
C120.32405 (10)0.59919 (16)0.29076 (4)0.0189 (2)
H120.29290.62940.31900.023*
C130.42150 (10)0.51030 (16)0.29039 (4)0.0182 (2)
C140.46702 (9)0.46835 (16)0.24731 (4)0.0185 (2)
H140.53250.41020.24630.022*
C150.41598 (9)0.51215 (16)0.20617 (4)0.0177 (2)
H150.44760.48310.17790.021*
C160.47564 (11)0.45835 (18)0.33516 (4)0.0251 (3)
H16A0.48020.56080.35520.038*
H16B0.54600.41490.32860.038*
H16C0.43520.36620.35030.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.01778 (15)0.02973 (16)0.01623 (13)−0.00376 (10)−0.00292 (9)−0.00163 (10)
Cl20.02586 (17)0.03750 (18)0.01277 (12)0.00235 (12)0.00091 (10)−0.00154 (10)
O10.0168 (4)0.0256 (4)0.0185 (4)0.0022 (3)−0.0001 (3)−0.0017 (3)
C10.0158 (5)0.0171 (5)0.0145 (4)0.0009 (4)−0.0025 (4)−0.0003 (3)
C20.0158 (5)0.0216 (5)0.0157 (4)0.0016 (4)0.0004 (4)0.0001 (4)
C30.0213 (6)0.0200 (5)0.0117 (4)0.0020 (4)−0.0010 (4)0.0007 (3)
C40.0183 (5)0.0210 (5)0.0156 (4)−0.0001 (4)−0.0043 (4)−0.0007 (4)
C50.0166 (5)0.0198 (5)0.0154 (4)−0.0007 (4)−0.0014 (4)0.0005 (4)
C60.0177 (5)0.0155 (4)0.0127 (4)0.0013 (4)−0.0010 (4)0.0012 (3)
C70.0191 (5)0.0152 (4)0.0153 (4)−0.0006 (4)0.0005 (4)−0.0008 (3)
C80.0188 (5)0.0172 (5)0.0144 (4)0.0018 (4)0.0001 (4)0.0001 (3)
C90.0170 (5)0.0173 (5)0.0159 (4)−0.0006 (4)0.0003 (4)−0.0001 (3)
C100.0177 (5)0.0163 (4)0.0127 (4)−0.0004 (4)0.0012 (4)−0.0001 (3)
C110.0180 (5)0.0200 (5)0.0156 (4)0.0021 (4)0.0006 (4)−0.0008 (4)
C120.0222 (6)0.0218 (5)0.0126 (4)0.0004 (4)0.0013 (4)−0.0008 (4)
C130.0204 (6)0.0184 (5)0.0158 (5)−0.0024 (4)−0.0019 (4)0.0007 (4)
C140.0168 (5)0.0207 (5)0.0179 (5)0.0013 (4)0.0002 (4)0.0001 (4)
C150.0175 (5)0.0209 (5)0.0149 (4)0.0013 (4)0.0009 (4)−0.0002 (4)
C160.0284 (7)0.0290 (6)0.0179 (5)0.0016 (5)−0.0058 (5)0.0011 (4)

Geometric parameters (Å, °)

Cl1—C11.7380 (11)C9—C101.4609 (15)
Cl2—C31.7360 (11)C9—H90.93
O1—C71.2228 (14)C10—C111.4008 (15)
C1—C21.3895 (15)C10—C151.4022 (17)
C1—C61.3957 (16)C11—C121.3871 (16)
C2—C31.3887 (16)C11—H110.93
C2—H20.93C12—C131.3919 (18)
C3—C41.3854 (17)C12—H120.93
C4—C51.3795 (15)C13—C141.4006 (16)
C4—H40.93C13—C161.5072 (16)
C5—C61.3971 (15)C14—C151.3855 (16)
C5—H50.93C14—H140.93
C6—C71.5077 (15)C15—H150.93
C7—C81.4725 (15)C16—H16A0.96
C8—C91.3424 (14)C16—H16B0.96
C8—H80.93C16—H16C0.96
C2—C1—C6122.08 (10)C10—C9—H9116.6
C2—C1—Cl1116.83 (9)C11—C10—C15118.00 (10)
C6—C1—Cl1120.90 (8)C11—C10—C9119.02 (10)
C3—C2—C1118.00 (11)C15—C10—C9122.98 (10)
C3—C2—H2121.0C12—C11—C10120.88 (11)
C1—C2—H2121.0C12—C11—H11119.6
C4—C3—C2121.92 (10)C10—C11—H11119.6
C4—C3—Cl2118.90 (9)C11—C12—C13121.12 (10)
C2—C3—Cl2119.15 (10)C11—C12—H12119.4
C5—C4—C3118.45 (10)C13—C12—H12119.4
C5—C4—H4120.8C12—C13—C14118.17 (10)
C3—C4—H4120.8C12—C13—C16120.83 (10)
C4—C5—C6122.15 (11)C14—C13—C16120.99 (11)
C4—C5—H5118.9C15—C14—C13121.00 (11)
C6—C5—H5118.9C15—C14—H14119.5
C1—C6—C5117.38 (10)C13—C14—H14119.5
C1—C6—C7125.90 (10)C14—C15—C10120.83 (10)
C5—C6—C7116.70 (10)C14—C15—H15119.6
O1—C7—C8122.79 (10)C10—C15—H15119.6
O1—C7—C6118.40 (10)C13—C16—H16A109.5
C8—C7—C6118.75 (10)C13—C16—H16B109.5
C9—C8—C7121.15 (11)H16A—C16—H16B109.5
C9—C8—H8119.4C13—C16—H16C109.5
C7—C8—H8119.4H16A—C16—H16C109.5
C8—C9—C10126.71 (11)H16B—C16—H16C109.5
C8—C9—H9116.6
C6—C1—C2—C30.00 (17)C5—C6—C7—C8141.55 (11)
Cl1—C1—C2—C3−175.09 (9)O1—C7—C8—C9−11.25 (18)
C1—C2—C3—C41.20 (17)C6—C7—C8—C9171.61 (10)
C1—C2—C3—Cl2179.44 (9)C7—C8—C9—C10−179.61 (11)
C2—C3—C4—C5−0.88 (17)C8—C9—C10—C11−177.16 (12)
Cl2—C3—C4—C5−179.12 (9)C8—C9—C10—C152.91 (19)
C3—C4—C5—C6−0.67 (17)C15—C10—C11—C12−0.83 (17)
C2—C1—C6—C5−1.44 (17)C9—C10—C11—C12179.24 (11)
Cl1—C1—C6—C5173.45 (9)C10—C11—C12—C130.09 (19)
C2—C1—C6—C7−179.70 (10)C11—C12—C13—C140.69 (18)
Cl1—C1—C6—C7−4.80 (16)C11—C12—C13—C16−178.42 (11)
C4—C5—C6—C11.79 (17)C12—C13—C14—C15−0.73 (18)
C4—C5—C6—C7−179.80 (10)C16—C13—C14—C15178.38 (11)
C1—C6—C7—O1142.55 (12)C13—C14—C15—C10−0.01 (18)
C5—C6—C7—O1−35.72 (15)C11—C10—C15—C140.79 (17)
C1—C6—C7—C8−40.19 (15)C9—C10—C15—C14−179.29 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.553.4352 (15)159
C8—H8···O1ii0.932.553.1995 (14)127
C11—H11···Cg1iii0.932.813.5611 (13)139
C14—H14···Cg1iv0.932.933.7066 (13)142

Symmetry codes: (i) x+1/2, −y+3/2, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, y+1/2, z; (iv) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2584).

References

  • Agrinskaya, N. V., Lukoshkin, V. A., Kudryavtsev, V. V., Nosova, G. I., Solovskaya, N. A. & Yakimanski, A. V. (1999). Phys. Solid State, 41, 1914–1917.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Gu, B., Ji, W., Patil, P. S., Dharmaprakash, S. M. & Wang, H. T. (2008). Appl. Phys. Lett.92, 091118–091120.
  • Patil, P. S., Dharmaprakash, S. M., Fun, H.-K. & Karthikeyan, M. S. (2006). J. Cryst. Growth, 297, 111–116.
  • Patil, P. S., Dharmaprakash, S. M., Ramakrishna, K., Fun, H.-K., Sai Santosh Kumar, R. & Rao, D. N. (2007). J. Cryst. Growth, 303, 520–524.
  • Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2122–o2123.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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