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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1951.
Published online 2008 September 17. doi:  10.1107/S1600536808029152
PMCID: PMC2959475

3-(5-Methyl-2-fur­yl)-1-(p-tol­yl)-2-propen-1-one

Abstract

The title compound, C15H14O2, was prepared from 4-methyl­hypnone and 5-methyl­furfural by Clasion–Schmidt condensation. All of the bond lengths and bond angles are in normal ranges. The dihedral angle formed by the benzene ring and furan ring is 5.31 (2).

Related literature

For the biological activity of chalcones, see: Hsieh et al. (1998 [triangle]); Anto et al. (1994 [triangle]). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000 [triangle]); Dimmock et al. (1998 [triangle]). For bond-length and angle data, see: Ali et al. (2005 [triangle]); Zhou (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1951-scheme1.jpg

Experimental

Crystal data

  • C15H14O2
  • M r = 226.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1951-efi1.jpg
  • a = 8.0394 (8) Å
  • b = 17.0278 (17) Å
  • c = 10.6550 (8) Å
  • β = 121.347 (6)°
  • V = 1245.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 (2) K
  • 0.2 × 0.2 × 0.2 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 7980 measured reflections
  • 2985 independent reflections
  • 1706 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.136
  • S = 1.02
  • 2985 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.11 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808029152/at2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029152/at2615Isup2.hkl

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

Acknowledgments

The authors thank the Natural Science Foundation of Wei Fang University (grant No. 2008Z04).

supplementary crystallographic information

Comment

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al.,1998) and antioxidant (Anto et al., 1994). Of particular interest, the effectiveness of chalcones against cancer has been investigated (De Vincenzo et al., 2000; Dimmock et al., 1998). As part of our search for new biologically active compounds we synthesized the title compound (I), and describe its structure here.

In the structure of (I) (Fig. 1), all of the bond lengths and bond angles fall in the normal range (Zhou, 2007; Ali et al., 2005). The dihedral angles formed by the benzene ring and furan ring is 5.31 (2)°. There are some weak C—H···O hydrogen bonds in the crystal structure (Table 1).

Experimental

A mixture of the 5-methylfurfural (0.02 mol), and 4-methylhypnone (0.02 mol) and 10% NaOH (10 ml) was stirred in ethanol (30 mL) for 3 h to afford the title compound (yield 85%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93-0.96 Å, and with Uiso=1.2–1.5Ueq.

Figures

Fig. 1.
The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C15H14O2F(000) = 480
Mr = 226.26Dx = 1.206 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1770 reflections
a = 8.0394 (8) Åθ = 0.4–27.5°
b = 17.0278 (17) ŵ = 0.08 mm1
c = 10.6550 (8) ÅT = 293 K
β = 121.347 (6)°Bar, colourless
V = 1245.7 (2) Å30.2 × 0.2 × 0.2 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1706 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 28.2°, θmin = 2.4°
phi and ω scansh = −8→10
7980 measured reflectionsk = −17→22
2985 independent reflectionsl = −13→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.136w = 1/[σ2(Fo2) + (0.0613P)2 + 0.0738P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2985 reflectionsΔρmax = 0.17 e Å3
155 parametersΔρmin = −0.11 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.011 (3)

Special details

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
O1−0.32694 (14)−0.22464 (6)−0.56944 (10)0.0574 (3)
O20.14482 (19)−0.01503 (7)−0.24561 (13)0.0810 (4)
C1−0.5507 (3)−0.33021 (11)−0.7020 (2)0.0892 (6)
H1A−0.6226−0.3521−0.79910.134*
H1B−0.6395−0.3140−0.67220.134*
H1C−0.4632−0.3691−0.63470.134*
C2−0.4379 (2)−0.26168 (9)−0.70182 (17)0.0582 (4)
C3−0.4181 (2)−0.22529 (10)−0.80412 (18)0.0656 (4)
H3A−0.4779−0.2393−0.90260.079*
C4−0.2899 (3)−0.16169 (10)−0.73553 (18)0.0665 (4)
H4A−0.2497−0.1259−0.78040.080*
C5−0.2364 (2)−0.16241 (8)−0.59293 (16)0.0545 (4)
C6−0.1121 (2)−0.11417 (9)−0.47132 (18)0.0590 (4)
H6A−0.0541−0.0723−0.49030.071*
C7−0.0686 (2)−0.12165 (9)−0.33318 (17)0.0577 (4)
H7A−0.1275−0.1613−0.30990.069*
C80.0699 (2)−0.06898 (9)−0.21687 (17)0.0591 (4)
C90.1224 (2)−0.08231 (9)−0.06208 (16)0.0558 (4)
C100.0379 (2)−0.13889 (10)−0.02027 (18)0.0683 (5)
H10A−0.0550−0.1724−0.09080.082*
C110.0888 (3)−0.14648 (11)0.1236 (2)0.0761 (5)
H11A0.0287−0.18500.14830.091*
C120.2260 (3)−0.09881 (10)0.23223 (19)0.0701 (5)
C130.3126 (3)−0.04334 (11)0.1911 (2)0.0802 (5)
H13A0.4077−0.01080.26240.096*
C140.2624 (3)−0.03474 (10)0.04727 (19)0.0734 (5)
H14A0.32350.00360.02310.088*
C150.2803 (3)−0.10657 (13)0.3896 (2)0.0940 (6)
H15A0.2064−0.14830.39790.141*
H15B0.2525−0.05820.42150.141*
H15C0.4168−0.11810.45000.141*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0672 (6)0.0599 (6)0.0517 (6)−0.0065 (5)0.0355 (5)−0.0031 (5)
O20.1026 (9)0.0684 (7)0.0750 (8)−0.0265 (7)0.0484 (7)−0.0067 (6)
C10.1063 (15)0.0854 (13)0.0788 (13)−0.0308 (11)0.0503 (11)−0.0160 (10)
C20.0607 (9)0.0627 (9)0.0534 (9)−0.0021 (7)0.0313 (7)−0.0068 (7)
C30.0744 (10)0.0738 (10)0.0502 (9)0.0001 (9)0.0335 (8)−0.0025 (8)
C40.0812 (11)0.0691 (10)0.0588 (10)−0.0043 (9)0.0430 (9)0.0049 (8)
C50.0587 (9)0.0546 (9)0.0566 (9)0.0013 (7)0.0345 (7)0.0025 (7)
C60.0630 (9)0.0544 (9)0.0658 (10)−0.0025 (7)0.0379 (8)−0.0015 (7)
C70.0614 (9)0.0544 (9)0.0602 (10)−0.0044 (7)0.0337 (8)−0.0019 (7)
C80.0624 (9)0.0513 (9)0.0649 (10)−0.0011 (7)0.0341 (8)−0.0021 (7)
C90.0567 (9)0.0517 (8)0.0568 (9)0.0029 (7)0.0280 (7)−0.0030 (7)
C100.0672 (10)0.0725 (11)0.0608 (11)−0.0082 (8)0.0302 (8)−0.0020 (8)
C110.0758 (12)0.0849 (12)0.0676 (12)−0.0017 (10)0.0374 (10)0.0088 (9)
C120.0721 (11)0.0747 (11)0.0597 (11)0.0223 (9)0.0315 (9)0.0060 (8)
C130.0872 (13)0.0762 (12)0.0610 (11)−0.0049 (10)0.0273 (10)−0.0138 (9)
C140.0856 (12)0.0631 (10)0.0683 (12)−0.0131 (9)0.0378 (10)−0.0096 (8)
C150.1016 (14)0.1128 (16)0.0632 (12)0.0270 (12)0.0398 (11)0.0108 (10)

Geometric parameters (Å, °)

O1—C21.3689 (17)C7—H7A0.9300
O1—C51.3800 (16)C8—C91.492 (2)
O2—C81.2218 (17)C9—C101.379 (2)
C1—C21.477 (2)C9—C141.384 (2)
C1—H1A0.9600C10—C111.372 (2)
C1—H1B0.9600C10—H10A0.9300
C1—H1C0.9600C11—C121.374 (2)
C2—C31.333 (2)C11—H11A0.9300
C3—C41.409 (2)C12—C131.374 (2)
C3—H3A0.9300C12—C151.503 (2)
C4—C51.347 (2)C13—C141.374 (2)
C4—H4A0.9300C13—H13A0.9300
C5—C61.416 (2)C14—H14A0.9300
C6—C71.330 (2)C15—H15A0.9600
C6—H6A0.9300C15—H15B0.9600
C7—C81.464 (2)C15—H15C0.9600
C2—O1—C5106.82 (11)O2—C8—C9119.91 (14)
C2—C1—H1A109.5C7—C8—C9119.74 (14)
C2—C1—H1B109.5C10—C9—C14117.28 (15)
H1A—C1—H1B109.5C10—C9—C8124.02 (14)
C2—C1—H1C109.5C14—C9—C8118.69 (15)
H1A—C1—H1C109.5C11—C10—C9121.08 (16)
H1B—C1—H1C109.5C11—C10—H10A119.5
C3—C2—O1109.70 (14)C9—C10—H10A119.5
C3—C2—C1134.46 (16)C10—C11—C12121.87 (17)
O1—C2—C1115.83 (13)C10—C11—H11A119.1
C2—C3—C4107.42 (15)C12—C11—H11A119.1
C2—C3—H3A126.3C11—C12—C13117.08 (17)
C4—C3—H3A126.3C11—C12—C15121.90 (18)
C5—C4—C3107.23 (14)C13—C12—C15121.02 (18)
C5—C4—H4A126.4C12—C13—C14121.72 (17)
C3—C4—H4A126.4C12—C13—H13A119.1
C4—C5—O1108.82 (13)C14—C13—H13A119.1
C4—C5—C6133.33 (14)C13—C14—C9120.96 (17)
O1—C5—C6117.85 (13)C13—C14—H14A119.5
C7—C6—C5127.68 (15)C9—C14—H14A119.5
C7—C6—H6A116.2C12—C15—H15A109.5
C5—C6—H6A116.2C12—C15—H15B109.5
C6—C7—C8121.64 (14)H15A—C15—H15B109.5
C6—C7—H7A119.2C12—C15—H15C109.5
C8—C7—H7A119.2H15A—C15—H15C109.5
O2—C8—C7120.35 (15)H15B—C15—H15C109.5

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2615).

References

  • Ali, H. M., Puvaneswary, S., Basirun, W. J. & Ng, S. W. (2005). Acta Cryst. E61, o1079–o1080.
  • Anto, R. J., Kuttan, G., Kuttan, R., Sathyanarayana, K. & Rao, M. N. A. (1994). J. Clin. Biochem. Nutr 17, 73–80.
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  • De Vincenzo, R., Ferlini, C., Distefano, M., Gaggini, C., Riva, A., Bombardelli, E., Morazzoni, P., Valenti, P., Belluti, F., Ranelletti, F. O., Mancuso, S. & Scambia, G. (2000). Cancer Chemother. Pharmacol.46, 305–312. [PubMed]
  • Dimmock, J. R., Kandepu, N. M., Hetherington, M., Quail, J. W., Pugazhenthi, U., Sudom, A. M., Chamankhah, M., Rose, P., Pass, E., Allen, T. M., Halleran, S., Szydlowski, J., Mutus, B., Tannous, M., Manavathu, E. K., Myers, T. G., De Clercq, E. & Balzarini, J. (1998). J. Med. Chem.41, 1014–1026. [PubMed]
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