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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1530.
Published online 2008 July 19. doi:  10.1107/S1600536808021934
PMCID: PMC2962155

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

Abstract

In the title mol­ecule, C13H9ClO2, the benzene and furyl rings are slightly twisted from each other with a dihedral angle of 5.1 (1)°. An intra­molecular C—H(...)O hydrogen-bond inter­action generates an S(5) ring motif. In the crystal structure, mol­ecules are stacked along the b axis and the crystal packing is stabilized by weak inter­molecular C—H(...)O hydrogen bonds.

Related literature

For related literature on the biological and nonlinear optical properties of chalcone derivatives, see: Agrinskaya et al. (1999 [triangle]); Chopra et al. (2007 [triangle]); DiCesare & Lakowicz (2000 [triangle]); Patil et al. (2006 [triangle], 2007 [triangle]); Gu, Ji, Patil & Dharmaprakash (2008 [triangle]); Gu, Ji, Patil, Dharmaprakash & Wang (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 [triangle]).

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Object name is e-64-o1530-scheme1.jpg

Experimental

Crystal data

  • C13H9ClO2
  • M r = 232.65
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1530-efi1.jpg
  • a = 21.3399 (7) Å
  • b = 3.7912 (1) Å
  • c = 12.9444 (4) Å
  • V = 1047.25 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 100.0 (1) K
  • 0.40 × 0.29 × 0.21 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.875, T max = 0.931
  • 13568 measured reflections
  • 5209 independent reflections
  • 4211 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.126
  • S = 1.08
  • 5209 reflections
  • 145 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.58 e Å−3
  • Δρmin = −0.28 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2227 Friedel pairs
  • Flack parameter: 0.07 (6)

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/S1600536808021934/lh2657sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021934/lh2657Isup2.hkl

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

Acknowledgments

HKF 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 a postdoctoral 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

Chalcone derivatives continue to attract the interest of chemists, biologists and physicists due to their remarkable biological and nonlinear optical properties (Chopra et al., 2007; DiCesare & Lakowicz, 2000; Patil, et al., 2006, 2007; Agrinskaya et al., 1999; Gu, Ji, Patil & Dharmaprakash, 2008; Gu, Ji, Patil, Dharmaprakash & Wang, 2008). We have synthesized the title compound (I) and its structure is reported here.

The bond lengths and bond angles in (I) have normal values (Allen et al., 1987). The benzene and furyl rings in the molecule are essentially planar with the maximum deviation from planarity being -0.003 (18)Å for atom C12 and -0.004 (14)Å for atom O1 respectively. The dihedral angle between the benzene and the furyl rings is 5.1 (1)°, indicating that they are only slightly twisted from each other.

An intramolecular C—H···O hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995). In the crystal structure, the molecules are are stacked along the b axis. The crystal packing is consolidated by C—H···O hydrogen bond interactions.

Experimental

The compound (I) was synthesized by the condensation of 4 -chlorobenzaldehyde (0.01 mol, 1.49 g m) with 2-acetylfuran (0.01 mol, 1.01 ml) 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 5 h. The resulting crude solid was filtered and dried. Then precipitated compound was recrystallized from N, N-dimethylformamide (DMF).

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. The dashed line indicates a hydrogen bond.
Fig. 2.
The crystal packing of the title compound, viewed along the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C13H9ClO2F000 = 480
Mr = 232.65Dx = 1.476 Mg m3
Orthorhombic, Pna21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4886 reflections
a = 21.3399 (7) Åθ = 2.5–37.2º
b = 3.79120 (10) ŵ = 0.34 mm1
c = 12.9444 (4) ÅT = 100.0 (1) K
V = 1047.25 (5) Å3Block, colourless
Z = 40.40 × 0.29 × 0.21 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer5209 independent reflections
Radiation source: fine-focus sealed tube4211 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 100.0(1) Kθmax = 38.2º
[var phi] and ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −31→37
Tmin = 0.875, Tmax = 0.931k = −6→6
13568 measured reflectionsl = −22→19

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047  w = 1/[σ2(Fo2) + (0.0686P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126(Δ/σ)max < 0.001
S = 1.08Δρmax = 0.58 e Å3
5209 reflectionsΔρmin = −0.27 e Å3
145 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 2216 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.07 (6)
Secondary atom site location: difference Fourier map

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
Cl10.249271 (17)0.53749 (9)0.21078 (5)0.02637 (9)
O10.03179 (5)0.2805 (3)0.94149 (7)0.0225 (2)
O20.00152 (6)0.1062 (3)0.74067 (9)0.0266 (2)
C10.06091 (7)0.3896 (4)1.02879 (11)0.0246 (3)
H1A0.04540.35571.09520.030*
C20.11562 (8)0.5548 (4)1.00653 (12)0.0243 (3)
H2A0.14370.65361.05330.029*
C30.12135 (7)0.5463 (4)0.89712 (12)0.0215 (3)
H3A0.15400.63880.85810.026*
C40.06937 (7)0.3752 (4)0.86037 (10)0.0192 (2)
C50.04991 (6)0.2723 (4)0.75621 (9)0.0198 (2)
C60.09349 (7)0.3737 (4)0.67253 (10)0.0202 (2)
H6A0.12740.51900.68750.024*
C70.08493 (6)0.2600 (4)0.57564 (10)0.0188 (2)
H7A0.04960.12230.56330.023*
C80.12568 (6)0.3314 (4)0.48732 (9)0.0178 (2)
C90.18485 (6)0.4918 (4)0.49906 (11)0.0188 (2)
H9A0.19840.55790.56450.023*
C100.22299 (7)0.5524 (4)0.41438 (11)0.0192 (2)
H10A0.26210.65770.42230.023*
C110.20160 (7)0.4524 (4)0.31741 (11)0.0186 (2)
C120.14356 (7)0.2960 (4)0.30286 (10)0.0198 (2)
H12A0.13010.23330.23700.024*
C130.10594 (6)0.2350 (4)0.38834 (9)0.0185 (2)
H13A0.06700.12840.37970.022*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.02847 (16)0.02869 (17)0.02196 (14)−0.00201 (13)0.00812 (11)0.00173 (17)
O10.0200 (4)0.0321 (6)0.0156 (4)0.0000 (4)0.0017 (3)0.0021 (4)
O20.0241 (5)0.0361 (6)0.0196 (4)−0.0065 (4)0.0001 (4)0.0017 (4)
C10.0265 (7)0.0314 (8)0.0161 (5)0.0055 (6)−0.0005 (5)−0.0023 (5)
C20.0268 (7)0.0249 (7)0.0211 (6)0.0033 (5)−0.0045 (5)−0.0027 (5)
C30.0201 (6)0.0220 (7)0.0223 (6)0.0000 (5)−0.0018 (5)0.0026 (5)
C40.0201 (5)0.0218 (6)0.0157 (5)0.0029 (5)0.0008 (4)0.0019 (4)
C50.0204 (6)0.0236 (6)0.0153 (5)0.0028 (5)0.0010 (4)0.0013 (4)
C60.0196 (5)0.0224 (6)0.0185 (5)−0.0008 (5)0.0010 (4)0.0006 (5)
C70.0186 (5)0.0197 (6)0.0181 (5)−0.0006 (5)0.0004 (4)0.0011 (4)
C80.0171 (5)0.0209 (6)0.0153 (5)0.0020 (5)−0.0006 (4)−0.0002 (4)
C90.0191 (5)0.0212 (6)0.0160 (5)0.0004 (5)−0.0007 (4)−0.0011 (4)
C100.0181 (6)0.0187 (6)0.0208 (5)−0.0012 (5)−0.0005 (4)0.0003 (5)
C110.0209 (6)0.0166 (6)0.0185 (5)0.0013 (5)0.0031 (4)0.0016 (4)
C120.0217 (6)0.0212 (6)0.0164 (5)−0.0006 (5)−0.0006 (4)−0.0014 (4)
C130.0173 (5)0.0218 (6)0.0164 (5)−0.0001 (5)−0.0023 (4)0.0004 (4)

Geometric parameters (Å, °)

Cl1—C111.7446 (14)C6—H6A0.9300
O1—C11.3543 (18)C7—C81.4617 (18)
O1—C41.3691 (16)C7—H7A0.9300
O2—C51.2261 (18)C8—C131.3974 (17)
C1—C21.356 (2)C8—C91.410 (2)
C1—H1A0.9300C9—C101.384 (2)
C2—C31.422 (2)C9—H9A0.9300
C2—H2A0.9300C10—C111.388 (2)
C3—C41.370 (2)C10—H10A0.9300
C3—H3A0.9300C11—C121.386 (2)
C4—C51.4637 (18)C12—C131.3865 (18)
C5—C61.4786 (18)C12—H12A0.9300
C6—C71.3388 (18)C13—H13A0.9300
C1—O1—C4106.93 (11)C6—C7—H7A116.9
O1—C1—C2111.03 (13)C8—C7—H7A116.9
O1—C1—H1A124.5C13—C8—C9118.80 (12)
C2—C1—H1A124.5C13—C8—C7119.30 (12)
C1—C2—C3105.97 (14)C9—C8—C7121.90 (11)
C1—C2—H2A127.0C10—C9—C8120.85 (12)
C3—C2—H2A127.0C10—C9—H9A119.6
C4—C3—C2106.68 (14)C8—C9—H9A119.6
C4—C3—H3A126.7C9—C10—C11118.51 (12)
C2—C3—H3A126.7C9—C10—H10A120.7
O1—C4—C3109.39 (12)C11—C10—H10A120.7
O1—C4—C5118.06 (12)C12—C11—C10122.24 (12)
C3—C4—C5132.51 (13)C12—C11—Cl1119.52 (11)
O2—C5—C4121.81 (12)C10—C11—Cl1118.23 (11)
O2—C5—C6122.90 (13)C11—C12—C13118.71 (12)
C4—C5—C6115.27 (12)C11—C12—H12A120.6
C7—C6—C5121.11 (13)C13—C12—H12A120.6
C7—C6—H6A119.4C12—C13—C8120.89 (12)
C5—C6—H6A119.4C12—C13—H13A119.6
C6—C7—C8126.29 (13)C8—C13—H13A119.6
C4—O1—C1—C20.69 (17)C5—C6—C7—C8−177.75 (13)
O1—C1—C2—C3−0.41 (18)C6—C7—C8—C13−171.24 (14)
C1—C2—C3—C4−0.02 (18)C6—C7—C8—C99.4 (2)
C1—O1—C4—C3−0.69 (16)C13—C8—C9—C10−0.2 (2)
C1—O1—C4—C5177.19 (12)C7—C8—C9—C10179.11 (14)
C2—C3—C4—O10.44 (17)C8—C9—C10—C110.2 (2)
C2—C3—C4—C5−177.02 (15)C9—C10—C11—C120.2 (2)
O1—C4—C5—O20.0 (2)C9—C10—C11—Cl1178.75 (11)
C3—C4—C5—O2177.28 (16)C10—C11—C12—C13−0.6 (2)
O1—C4—C5—C6−178.30 (12)Cl1—C11—C12—C13−179.09 (11)
C3—C4—C5—C6−1.0 (2)C11—C12—C13—C80.5 (2)
O2—C5—C6—C7−6.2 (2)C9—C8—C13—C12−0.2 (2)
C4—C5—C6—C7172.11 (14)C7—C8—C13—C12−179.49 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7A···O20.932.522.8411 (17)101
C13—H13A···O2i0.932.483.2535 (18)140

Symmetry codes: (i) −x, −y, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2657).

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.
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  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
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  • Gu, B., Ji, W., Patil, P. S., Dharmaprakash, S. M. & Wang, H. T. (2008). Appl. Phys. Lett.92, 091118.
  • 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.
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