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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1177.
Published online 2008 May 30. doi:  10.1107/S1600536808015420
PMCID: PMC2961505

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

Abstract

The title compound, C15H10Cl2O, adopts an E configuration with respect to the C=C bond of the propenone unit. The dihedral angle between the two benzene rings is 32.4 (1)°. Intra­molecular C—H(...)O and C—H(...)Cl hydrogen bonds generate an S(5)S(5)S(5) motif. In addition, the crystal structure is stabilized by weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For related literature on chalcones, see: Fun et al. (2007 [triangle]); Patil et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For graph-set motifs, see: Bernstein et al. (1995 [triangle]).

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Object name is e-64-o1177-scheme1.jpg

Experimental

Crystal data

  • C15H10Cl2O
  • M r = 277.13
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1177-efi1.jpg
  • a = 7.2777 (1) Å
  • b = 11.2686 (2) Å
  • c = 30.2365 (6) Å
  • V = 2479.68 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.51 mm−1
  • T = 100.0 (1) K
  • 0.51 × 0.34 × 0.19 mm

Data collection

  • Bruker SMART APEX2 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.781, T max = 0.911
  • 42713 measured reflections
  • 5996 independent reflections
  • 4413 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.127
  • S = 1.05
  • 5996 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.21 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/S1600536808015420/lh2627sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015420/lh2627Isup2.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. HKF and IAR also thank the Malaysian Government and Universiti Sains Malaysia for FRGS grant No. 203/PFIZIK/671064. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship. This work was supported by the Department of Science and Technology (DST), Government of India (grant No. SR/S2/LOP-17/2006).

supplementary crystallographic information

Comment

In continuation of our study on chalcone derivatives (Fun et al., 2007; Patil et al., 2007), the crystal structure of the title compound (I) is reported herein.

In (I), the molecule exhibits an E configuration with respect to the C8═C9 double bond with the C7–C8–C9–C10 torsion angle being 163.0 (2) °. The bond lengths in the title compound (Fig. 1) have normal values (Allen et al., 1987). The dihedral angle between the two benzene rings is 32.7 (1)°.

Intramolecular C—H···O and C-H···Cl hydrogen bonds generate an S(5)S(5)S(5) motif (Bernstein et al., 1995). In addition, the crystal structure is stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1).

Experimental

The compound (I) was synthesized by the condensation of 2 -chlorobenzaldehyde (0.01 mol) with 4-chloroacetophenones (0.01 mol) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring (6 h), the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 12 h. The resulting crude solid was filtered 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 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Figures

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

Crystal data

C15H10Cl2OF000 = 1136
Mr = 277.13Dx = 1.485 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8869 reflections
a = 7.2777 (1) Åθ = 2.7–36.0º
b = 11.2686 (2) ŵ = 0.51 mm1
c = 30.2365 (6) ÅT = 100.0 (1) K
V = 2479.68 (7) Å3Block, colourless
Z = 80.51 × 0.34 × 0.19 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer5996 independent reflections
Radiation source: fine-focus sealed tube4413 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
T = 100.0(1) Kθmax = 36.4º
[var phi] and ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −7→12
Tmin = 0.781, Tmax = 0.911k = −17→18
42713 measured reflectionsl = −50→48

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) = 0.127  w = 1/[σ2(Fo2) + (0.0601P)2 + 0.6003P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
5996 reflectionsΔρmax = 0.55 e Å3
163 parametersΔρmin = −0.21 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
Cl10.92678 (5)0.49110 (3)0.058017 (10)0.02768 (8)
Cl21.06791 (4)0.29033 (3)0.406266 (11)0.02816 (8)
O11.19326 (15)0.53008 (8)0.20697 (3)0.0293 (2)
C10.99869 (17)0.34415 (10)0.06050 (4)0.0217 (2)
C20.9725 (2)0.27399 (11)0.02335 (4)0.0261 (2)
H2A0.92330.3066−0.00230.031*
C31.0200 (2)0.15500 (11)0.02468 (5)0.0295 (3)
H3A1.00320.1074−0.00010.035*
C41.0934 (2)0.10670 (11)0.06340 (5)0.0277 (3)
H4A1.12500.02680.06440.033*
C51.11899 (19)0.17750 (10)0.10012 (4)0.0247 (2)
H5A1.16820.14430.12570.030*
C61.07237 (16)0.29880 (10)0.09989 (4)0.0214 (2)
C71.10257 (17)0.37394 (10)0.13844 (4)0.0229 (2)
H7A1.10070.45550.13370.028*
C81.13268 (18)0.33788 (10)0.17986 (4)0.0245 (2)
H8A1.13640.25720.18630.029*
C91.16008 (17)0.42575 (10)0.21552 (4)0.0226 (2)
C101.14122 (17)0.38733 (10)0.26259 (4)0.0212 (2)
C111.10474 (19)0.27011 (11)0.27512 (4)0.0258 (2)
H11A1.09480.21160.25360.031*
C121.08325 (18)0.24012 (11)0.31927 (5)0.0260 (2)
H12A1.05830.16220.32740.031*
C131.09944 (16)0.32798 (10)0.35122 (4)0.0227 (2)
C141.13629 (18)0.44474 (11)0.33986 (4)0.0247 (2)
H14A1.14710.50280.36160.030*
C151.15668 (18)0.47343 (10)0.29565 (4)0.0239 (2)
H15A1.18120.55160.28780.029*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.03936 (18)0.01927 (12)0.02440 (15)0.00338 (11)0.00267 (12)0.00341 (9)
Cl20.03176 (16)0.02708 (15)0.02565 (15)−0.00451 (12)0.00190 (11)−0.00078 (10)
O10.0399 (5)0.0181 (4)0.0299 (5)−0.0008 (4)−0.0062 (4)0.0006 (3)
C10.0255 (5)0.0174 (4)0.0223 (5)−0.0004 (4)0.0031 (4)0.0014 (4)
C20.0355 (6)0.0228 (5)0.0201 (5)−0.0030 (5)0.0029 (5)0.0015 (4)
C30.0414 (7)0.0213 (5)0.0260 (6)−0.0050 (5)0.0034 (5)−0.0026 (4)
C40.0362 (7)0.0171 (5)0.0299 (6)−0.0008 (5)0.0012 (5)−0.0016 (4)
C50.0283 (6)0.0187 (5)0.0272 (6)0.0014 (5)−0.0011 (5)0.0006 (4)
C60.0219 (5)0.0186 (5)0.0236 (5)−0.0010 (4)0.0011 (4)−0.0007 (4)
C70.0243 (5)0.0181 (4)0.0263 (6)0.0003 (4)−0.0021 (4)−0.0009 (4)
C80.0283 (6)0.0194 (5)0.0258 (6)0.0015 (4)−0.0022 (5)−0.0022 (4)
C90.0244 (5)0.0182 (4)0.0253 (6)0.0022 (4)−0.0042 (4)−0.0015 (4)
C100.0217 (5)0.0158 (4)0.0262 (6)0.0014 (4)−0.0026 (4)−0.0028 (4)
C110.0324 (6)0.0178 (5)0.0272 (6)−0.0002 (5)−0.0003 (5)−0.0051 (4)
C120.0309 (6)0.0174 (4)0.0295 (6)−0.0016 (4)0.0018 (5)−0.0020 (4)
C130.0223 (5)0.0208 (5)0.0251 (6)−0.0002 (4)−0.0007 (4)−0.0015 (4)
C140.0281 (6)0.0195 (5)0.0264 (6)−0.0012 (5)−0.0032 (5)−0.0039 (4)
C150.0274 (5)0.0168 (4)0.0275 (6)−0.0004 (4)−0.0045 (5)−0.0019 (4)

Geometric parameters (Å, °)

Cl1—C11.7383 (12)C7—H7A0.9300
Cl2—C131.7330 (13)C8—C91.4775 (17)
O1—C91.2277 (14)C8—H8A0.9300
C1—C21.3868 (18)C9—C101.4939 (18)
C1—C61.4024 (17)C10—C151.3975 (16)
C2—C31.3854 (18)C10—C111.3997 (17)
C2—H2A0.9300C11—C121.3857 (19)
C3—C41.397 (2)C11—H11A0.9300
C3—H3A0.9300C12—C131.3883 (18)
C4—C51.3800 (18)C12—H12A0.9300
C4—H4A0.9300C13—C141.3860 (17)
C5—C61.4084 (16)C14—C151.3834 (19)
C5—H5A0.9300C14—H14A0.9300
C6—C71.4574 (17)C15—H15A0.9300
C7—C81.3347 (18)
C2—C1—C6122.19 (11)C9—C8—H8A119.9
C2—C1—Cl1117.81 (10)O1—C9—C8120.97 (12)
C6—C1—Cl1119.93 (9)O1—C9—C10119.75 (11)
C3—C2—C1119.60 (12)C8—C9—C10119.25 (10)
C3—C2—H2A120.2C15—C10—C11118.47 (12)
C1—C2—H2A120.2C15—C10—C9118.22 (10)
C2—C3—C4119.79 (12)C11—C10—C9123.29 (11)
C2—C3—H3A120.1C12—C11—C10120.83 (11)
C4—C3—H3A120.1C12—C11—H11A119.6
C5—C4—C3120.04 (12)C10—C11—H11A119.6
C5—C4—H4A120.0C11—C12—C13119.13 (11)
C3—C4—H4A120.0C11—C12—H12A120.4
C4—C5—C6121.64 (12)C13—C12—H12A120.4
C4—C5—H5A119.2C14—C13—C12121.40 (12)
C6—C5—H5A119.2C14—C13—Cl2119.73 (10)
C1—C6—C5116.74 (11)C12—C13—Cl2118.85 (10)
C1—C6—C7121.68 (10)C15—C14—C13118.81 (11)
C5—C6—C7121.57 (11)C15—C14—H14A120.6
C8—C7—C6126.75 (11)C13—C14—H14A120.6
C8—C7—H7A116.6C14—C15—C10121.36 (11)
C6—C7—H7A116.6C14—C15—H15A119.3
C7—C8—C9120.19 (11)C10—C15—H15A119.3
C7—C8—H8A119.9
C6—C1—C2—C30.0 (2)C7—C8—C9—C10163.02 (12)
Cl1—C1—C2—C3−177.01 (11)O1—C9—C10—C151.95 (18)
C1—C2—C3—C40.2 (2)C8—C9—C10—C15−176.18 (11)
C2—C3—C4—C5−0.3 (2)O1—C9—C10—C11−179.57 (13)
C3—C4—C5—C60.2 (2)C8—C9—C10—C112.31 (18)
C2—C1—C6—C5−0.06 (18)C15—C10—C11—C120.40 (19)
Cl1—C1—C6—C5176.87 (10)C9—C10—C11—C12−178.08 (12)
C2—C1—C6—C7178.80 (12)C10—C11—C12—C13−0.4 (2)
Cl1—C1—C6—C7−4.27 (16)C11—C12—C13—C140.09 (19)
C4—C5—C6—C1−0.02 (19)C11—C12—C13—Cl2178.74 (10)
C4—C5—C6—C7−178.88 (12)C12—C13—C14—C150.16 (19)
C1—C6—C7—C8164.24 (13)Cl2—C13—C14—C15−178.48 (10)
C5—C6—C7—C8−17.0 (2)C13—C14—C15—C10−0.13 (19)
C6—C7—C8—C9−179.71 (12)C11—C10—C15—C14−0.15 (19)
C7—C8—C9—O1−15.08 (19)C9—C10—C15—C14178.41 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7A···Cl10.932.653.0484 (12)107
C7—H7A···O10.932.462.7973 (15)101
C15—H15A···O10.932.462.7691 (15)100
C12—H12A···O1i0.932.593.2064 (16)125

Symmetry codes: (i) −x+2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2627).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fun, H.-K., Chantrapromma, S., Patil, P. S. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2724–o2725.
  • Patil, P. S., Fun, H.-K., Chantrapromma, S. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2497–o2498.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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