Acta Cryst. (2008). E64, o1951 [ doi:10.1107/S1600536808029152 ]
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).
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.
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.
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./at2615fig1thm.gif)
| Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
| C15H14O2 | F(000) = 480 |
| Mr = 226.26 | Dx = 1.206 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 1770 reflections |
| a = 8.0394 (8) Å | θ = 0.4–27.5° |
| b = 17.0278 (17) Å | µ = 0.08 mm−1 |
| c = 10.6550 (8) Å | T = 293 K |
| β = 121.347 (6)° | Bar, colourless |
| V = 1245.7 (2) Å3 | 0.2 × 0.2 × 0.2 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 1706 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.026 |
| graphite | θmax = 28.2°, θmin = 2.4° |
| phi and ω scans | h = −8→10 |
| 7980 measured reflections | k = −17→22 |
| 2985 independent reflections | l = −13→13 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.0613P)2 + 0.0738P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.02 | (Δ/σ)max < 0.001 |
| 2985 reflections | Δρmax = 0.17 e Å−3 |
| 155 parameters | Δρmin = −0.11 e Å−3 |
| 0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (3) |
| C15H14O2 | V = 1245.7 (2) Å3 |
| Mr = 226.26 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 8.0394 (8) Å | µ = 0.08 mm−1 |
| b = 17.0278 (17) Å | T = 293 K |
| c = 10.6550 (8) Å | 0.2 × 0.2 × 0.2 mm |
| β = 121.347 (6)° |
| Bruker SMART CCD area-detector diffractometer | 1706 reflections with I > 2σ(I) |
| 7980 measured reflections | Rint = 0.026 |
| 2985 independent reflections | θmax = 28.2° |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.136 | Δρmax = 0.17 e Å−3 |
| S = 1.02 | Δρmin = −0.11 e Å−3 |
| 2985 reflections | Absolute structure: ? |
| 155 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | −0.32694 (14) | −0.22464 (6) | −0.56944 (10) | 0.0574 (3) | |
| O2 | 0.14482 (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 | −0.7991 | 0.134* | |
| H1B | −0.6395 | −0.3140 | −0.6722 | 0.134* | |
| H1C | −0.4632 | −0.3691 | −0.6347 | 0.134* | |
| 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 | −0.9026 | 0.079* | |
| C4 | −0.2899 (3) | −0.16169 (10) | −0.73553 (18) | 0.0665 (4) | |
| H4A | −0.2497 | −0.1259 | −0.7804 | 0.080* | |
| 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 | −0.4903 | 0.071* | |
| C7 | −0.0686 (2) | −0.12165 (9) | −0.33318 (17) | 0.0577 (4) | |
| H7A | −0.1275 | −0.1613 | −0.3099 | 0.069* | |
| C8 | 0.0699 (2) | −0.06898 (9) | −0.21687 (17) | 0.0591 (4) | |
| C9 | 0.1224 (2) | −0.08231 (9) | −0.06208 (16) | 0.0558 (4) | |
| C10 | 0.0379 (2) | −0.13889 (10) | −0.02027 (18) | 0.0683 (5) | |
| H10A | −0.0550 | −0.1724 | −0.0908 | 0.082* | |
| C11 | 0.0888 (3) | −0.14648 (11) | 0.1236 (2) | 0.0761 (5) | |
| H11A | 0.0287 | −0.1850 | 0.1483 | 0.091* | |
| C12 | 0.2260 (3) | −0.09881 (10) | 0.23223 (19) | 0.0701 (5) | |
| C13 | 0.3126 (3) | −0.04334 (11) | 0.1911 (2) | 0.0802 (5) | |
| H13A | 0.4077 | −0.0108 | 0.2624 | 0.096* | |
| C14 | 0.2624 (3) | −0.03474 (10) | 0.04727 (19) | 0.0734 (5) | |
| H14A | 0.3235 | 0.0036 | 0.0231 | 0.088* | |
| C15 | 0.2803 (3) | −0.10657 (13) | 0.3896 (2) | 0.0940 (6) | |
| H15A | 0.2064 | −0.1483 | 0.3979 | 0.141* | |
| H15B | 0.2525 | −0.0582 | 0.4215 | 0.141* | |
| H15C | 0.4168 | −0.1181 | 0.4500 | 0.141* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0672 (6) | 0.0599 (6) | 0.0517 (6) | −0.0065 (5) | 0.0355 (5) | −0.0031 (5) |
| O2 | 0.1026 (9) | 0.0684 (7) | 0.0750 (8) | −0.0265 (7) | 0.0484 (7) | −0.0067 (6) |
| C1 | 0.1063 (15) | 0.0854 (13) | 0.0788 (13) | −0.0308 (11) | 0.0503 (11) | −0.0160 (10) |
| C2 | 0.0607 (9) | 0.0627 (9) | 0.0534 (9) | −0.0021 (7) | 0.0313 (7) | −0.0068 (7) |
| C3 | 0.0744 (10) | 0.0738 (10) | 0.0502 (9) | 0.0001 (9) | 0.0335 (8) | −0.0025 (8) |
| C4 | 0.0812 (11) | 0.0691 (10) | 0.0588 (10) | −0.0043 (9) | 0.0430 (9) | 0.0049 (8) |
| C5 | 0.0587 (9) | 0.0546 (9) | 0.0566 (9) | 0.0013 (7) | 0.0345 (7) | 0.0025 (7) |
| C6 | 0.0630 (9) | 0.0544 (9) | 0.0658 (10) | −0.0025 (7) | 0.0379 (8) | −0.0015 (7) |
| C7 | 0.0614 (9) | 0.0544 (9) | 0.0602 (10) | −0.0044 (7) | 0.0337 (8) | −0.0019 (7) |
| C8 | 0.0624 (9) | 0.0513 (9) | 0.0649 (10) | −0.0011 (7) | 0.0341 (8) | −0.0021 (7) |
| C9 | 0.0567 (9) | 0.0517 (8) | 0.0568 (9) | 0.0029 (7) | 0.0280 (7) | −0.0030 (7) |
| C10 | 0.0672 (10) | 0.0725 (11) | 0.0608 (11) | −0.0082 (8) | 0.0302 (8) | −0.0020 (8) |
| C11 | 0.0758 (12) | 0.0849 (12) | 0.0676 (12) | −0.0017 (10) | 0.0374 (10) | 0.0088 (9) |
| C12 | 0.0721 (11) | 0.0747 (11) | 0.0597 (11) | 0.0223 (9) | 0.0315 (9) | 0.0060 (8) |
| C13 | 0.0872 (13) | 0.0762 (12) | 0.0610 (11) | −0.0049 (10) | 0.0273 (10) | −0.0138 (9) |
| C14 | 0.0856 (12) | 0.0631 (10) | 0.0683 (12) | −0.0131 (9) | 0.0378 (10) | −0.0096 (8) |
| C15 | 0.1016 (14) | 0.1128 (16) | 0.0632 (12) | 0.0270 (12) | 0.0398 (11) | 0.0108 (10) |
| O1—C2 | 1.3689 (17) | C7—H7A | 0.9300 |
| O1—C5 | 1.3800 (16) | C8—C9 | 1.492 (2) |
| O2—C8 | 1.2218 (17) | C9—C10 | 1.379 (2) |
| C1—C2 | 1.477 (2) | C9—C14 | 1.384 (2) |
| C1—H1A | 0.9600 | C10—C11 | 1.372 (2) |
| C1—H1B | 0.9600 | C10—H10A | 0.9300 |
| C1—H1C | 0.9600 | C11—C12 | 1.374 (2) |
| C2—C3 | 1.333 (2) | C11—H11A | 0.9300 |
| C3—C4 | 1.409 (2) | C12—C13 | 1.374 (2) |
| C3—H3A | 0.9300 | C12—C15 | 1.503 (2) |
| C4—C5 | 1.347 (2) | C13—C14 | 1.374 (2) |
| C4—H4A | 0.9300 | C13—H13A | 0.9300 |
| C5—C6 | 1.416 (2) | C14—H14A | 0.9300 |
| C6—C7 | 1.330 (2) | C15—H15A | 0.9600 |
| C6—H6A | 0.9300 | C15—H15B | 0.9600 |
| C7—C8 | 1.464 (2) | C15—H15C | 0.9600 |
| C2—O1—C5 | 106.82 (11) | O2—C8—C9 | 119.91 (14) |
| C2—C1—H1A | 109.5 | C7—C8—C9 | 119.74 (14) |
| C2—C1—H1B | 109.5 | C10—C9—C14 | 117.28 (15) |
| H1A—C1—H1B | 109.5 | C10—C9—C8 | 124.02 (14) |
| C2—C1—H1C | 109.5 | C14—C9—C8 | 118.69 (15) |
| H1A—C1—H1C | 109.5 | C11—C10—C9 | 121.08 (16) |
| H1B—C1—H1C | 109.5 | C11—C10—H10A | 119.5 |
| C3—C2—O1 | 109.70 (14) | C9—C10—H10A | 119.5 |
| C3—C2—C1 | 134.46 (16) | C10—C11—C12 | 121.87 (17) |
| O1—C2—C1 | 115.83 (13) | C10—C11—H11A | 119.1 |
| C2—C3—C4 | 107.42 (15) | C12—C11—H11A | 119.1 |
| C2—C3—H3A | 126.3 | C11—C12—C13 | 117.08 (17) |
| C4—C3—H3A | 126.3 | C11—C12—C15 | 121.90 (18) |
| C5—C4—C3 | 107.23 (14) | C13—C12—C15 | 121.02 (18) |
| C5—C4—H4A | 126.4 | C12—C13—C14 | 121.72 (17) |
| C3—C4—H4A | 126.4 | C12—C13—H13A | 119.1 |
| C4—C5—O1 | 108.82 (13) | C14—C13—H13A | 119.1 |
| C4—C5—C6 | 133.33 (14) | C13—C14—C9 | 120.96 (17) |
| O1—C5—C6 | 117.85 (13) | C13—C14—H14A | 119.5 |
| C7—C6—C5 | 127.68 (15) | C9—C14—H14A | 119.5 |
| C7—C6—H6A | 116.2 | C12—C15—H15A | 109.5 |
| C5—C6—H6A | 116.2 | C12—C15—H15B | 109.5 |
| C6—C7—C8 | 121.64 (14) | H15A—C15—H15B | 109.5 |
| C6—C7—H7A | 119.2 | C12—C15—H15C | 109.5 |
| C8—C7—H7A | 119.2 | H15A—C15—H15C | 109.5 |
| O2—C8—C7 | 120.35 (15) | H15B—C15—H15C | 109.5 |
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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).