supplementary materials
(E)-3-(2-Furyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
In the title molecule, C13H10O3, an intramolecular O-H
O hydrogen bond influences the molecular conformation, and the benzene and furan rings form a dihedral angle of 8.35 (7)°. Weak intermolecular C-HO hydrogen bonds link molecules into sheets parallel to the bc plane.
Furan-2-carbaldehyde (0.3 mmol) and 2-hydroxylacetophenone (0.3 mmol), NaOH (0.3 mmol) were mixed in 50 ml flash under sovlent-free conditions After
stirring for 5 min at 373 K, the mixture was soilden slowly and afforded the title compound,
then recrystallized from ethanol, affording the title compound as a colourless
crystalline solid. Elemental analysis: calculated for C13H10O3: C 72.90,
H 4.71%; found: C 72.88, H 4.65%.
All H atoms were placed in geometrically idealized positions (O—H 0.85 Å,
C—H 0.93 Å) and treated as riding, with
Uiso(H) = 1.2 Ueq(C,O).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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).
(E)-3-(2-Furyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
top
Crystal data top
| C13H10O3 | F(000) = 448 |
| Mr = 214.21 | Dx = 1.367 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 3.8560 (5) Å | Cell parameters from 438 reflections |
| b = 15.6565 (14) Å | θ = 2.4–18.4° |
| c = 17.309 (2) Å | µ = 0.10 mm−1 |
| β = 95.065 (2)° | T = 298 K |
| V = 1040.9 (2) Å3 | Block, colourless |
| Z = 4 | 0.27 × 0.25 × 0.07 mm |
Data collection top
Siemens SMART CCD area-detector
diffractometer | 1848 independent reflections |
| Radiation source: fine-focus sealed tube | 668 reflections with I > 2σ(I) |
| graphite | Rint = 0.126 |
| Detector resolution: φ and ω pixels mm-1 | θmax = 25.0°, θmin = 1.8° |
| φ and ω scans | h = −4→4 |
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996) | k = −7→18 |
| Tmin = 0.974, Tmax = 0.993 | l = −20→20 |
| 5153 measured reflections | |
Refinement top
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.184 | H-atom parameters constrained |
| S = 0.81 | w = 1/[σ2(Fo2) + (0.0721P)2]
where P = (Fo2 + 2Fc2)/3 |
| 1848 reflections | (Δ/σ)max < 0.001 |
| 146 parameters | Δρmax = 0.22 e Å−3 |
| 0 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
| C13H10O3 | V = 1040.9 (2) Å3 |
| Mr = 214.21 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 3.8560 (5) Å | µ = 0.10 mm−1 |
| b = 15.6565 (14) Å | T = 298 K |
| c = 17.309 (2) Å | 0.27 × 0.25 × 0.07 mm |
| β = 95.065 (2)° | |
Data collection top
Siemens SMART CCD area-detector
diffractometer | 1848 independent reflections |
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996) | 668 reflections with I > 2σ(I) |
| Tmin = 0.974, Tmax = 0.993 | Rint = 0.126 |
| 5153 measured reflections | θmax = 25.0° |
Refinement top
| R[F2 > 2σ(F2)] = 0.067 | H-atom parameters constrained |
| wR(F2) = 0.184 | Δρmax = 0.22 e Å−3 |
| S = 0.81 | Δρmin = −0.19 e Å−3 |
| 1848 reflections | Absolute structure: ? |
| 146 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Special details top
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) top| | x | y | z | Uiso*/Ueq | |
| O1 | 1.0561 (7) | 0.73465 (16) | 0.48262 (15) | 0.0794 (9) | |
| O2 | 0.8017 (8) | 0.83794 (18) | 0.74522 (15) | 0.0885 (11) | |
| O3 | 0.5477 (10) | 0.9672 (2) | 0.80912 (17) | 0.1030 (12) | |
| H3 | 0.6546 | 0.9220 | 0.8087 | 0.154* | |
| C1 | 1.1454 (12) | 0.6735 (3) | 0.4327 (2) | 0.0842 (15) | |
| H1 | 1.1472 | 0.6811 | 0.3794 | 0.101* | |
| C2 | 1.2297 (11) | 0.6018 (3) | 0.4699 (3) | 0.0769 (13) | |
| H2 | 1.3018 | 0.5510 | 0.4485 | 0.092* | |
| C3 | 1.1887 (11) | 0.6177 (3) | 0.5478 (2) | 0.0748 (13) | |
| H3A | 1.2271 | 0.5788 | 0.5882 | 0.090* | |
| C4 | 1.0842 (10) | 0.6991 (2) | 0.5544 (2) | 0.0584 (10) | |
| C5 | 0.9983 (9) | 0.7493 (2) | 0.6177 (2) | 0.0608 (11) | |
| H5 | 1.0222 | 0.7240 | 0.6665 | 0.073* | |
| C6 | 0.8860 (10) | 0.8300 (2) | 0.6137 (2) | 0.0598 (11) | |
| H6 | 0.8676 | 0.8578 | 0.5661 | 0.072* | |
| C7 | 0.7918 (10) | 0.8754 (2) | 0.6822 (2) | 0.0600 (11) | |
| C8 | 0.6700 (9) | 0.9648 (2) | 0.6757 (2) | 0.0553 (10) | |
| C9 | 0.5559 (11) | 1.0064 (3) | 0.7399 (2) | 0.0690 (12) | |
| C10 | 0.4467 (12) | 1.0901 (3) | 0.7358 (3) | 0.0835 (14) | |
| H10 | 0.3697 | 1.1170 | 0.7790 | 0.100* | |
| C11 | 0.4529 (13) | 1.1329 (3) | 0.6679 (3) | 0.0930 (16) | |
| H11 | 0.3769 | 1.1893 | 0.6649 | 0.112* | |
| C12 | 0.5685 (12) | 1.0951 (3) | 0.6033 (3) | 0.0839 (14) | |
| H12 | 0.5747 | 1.1256 | 0.5573 | 0.101* | |
| C13 | 0.6745 (11) | 1.0117 (3) | 0.6079 (2) | 0.0702 (12) | |
| H13 | 0.7518 | 0.9858 | 0.5642 | 0.084* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O1 | 0.111 (3) | 0.0632 (19) | 0.0648 (18) | 0.0106 (16) | 0.0132 (16) | −0.0022 (16) |
| O2 | 0.138 (3) | 0.067 (2) | 0.0625 (18) | 0.0095 (18) | 0.0190 (18) | 0.0029 (15) |
| O3 | 0.150 (4) | 0.087 (3) | 0.076 (2) | 0.010 (2) | 0.033 (2) | −0.0105 (18) |
| C1 | 0.112 (4) | 0.076 (3) | 0.065 (3) | 0.008 (3) | 0.015 (3) | −0.014 (3) |
| C2 | 0.080 (4) | 0.057 (3) | 0.095 (3) | 0.008 (2) | 0.012 (3) | −0.016 (3) |
| C3 | 0.086 (4) | 0.061 (3) | 0.078 (3) | 0.008 (2) | 0.011 (2) | −0.004 (2) |
| C4 | 0.065 (3) | 0.053 (2) | 0.058 (2) | −0.002 (2) | 0.010 (2) | −0.001 (2) |
| C5 | 0.063 (3) | 0.059 (2) | 0.061 (2) | 0.001 (2) | 0.010 (2) | 0.004 (2) |
| C6 | 0.067 (3) | 0.058 (2) | 0.054 (2) | 0.002 (2) | 0.005 (2) | −0.003 (2) |
| C7 | 0.064 (3) | 0.057 (3) | 0.059 (2) | −0.005 (2) | 0.004 (2) | 0.001 (2) |
| C8 | 0.055 (3) | 0.053 (2) | 0.058 (2) | −0.0020 (19) | 0.006 (2) | −0.001 (2) |
| C9 | 0.071 (3) | 0.069 (3) | 0.068 (3) | −0.001 (2) | 0.009 (2) | −0.009 (2) |
| C10 | 0.080 (4) | 0.073 (3) | 0.095 (4) | 0.008 (3) | 0.001 (3) | −0.023 (3) |
| C11 | 0.093 (4) | 0.061 (3) | 0.122 (4) | 0.014 (3) | −0.014 (3) | −0.013 (3) |
| C12 | 0.099 (4) | 0.063 (3) | 0.086 (3) | 0.000 (3) | −0.008 (3) | 0.007 (3) |
| C13 | 0.078 (3) | 0.056 (3) | 0.076 (3) | −0.004 (2) | 0.007 (2) | −0.005 (2) |
Geometric parameters (Å, °) top
| O1—C1 | 1.354 (4) | C6—C7 | 1.455 (5) |
| O1—C4 | 1.357 (4) | C6—H6 | 0.9300 |
| O2—C7 | 1.237 (4) | C7—C8 | 1.476 (5) |
| O3—C9 | 1.349 (4) | C8—C13 | 1.386 (5) |
| O3—H3 | 0.8200 | C8—C9 | 1.393 (5) |
| C1—C2 | 1.321 (5) | C9—C10 | 1.377 (6) |
| C1—H1 | 0.9300 | C10—C11 | 1.354 (5) |
| C2—C3 | 1.394 (5) | C10—H10 | 0.9300 |
| C2—H2 | 0.9300 | C11—C12 | 1.374 (6) |
| C3—C4 | 1.343 (5) | C11—H11 | 0.9300 |
| C3—H3A | 0.9300 | C12—C13 | 1.368 (5) |
| C4—C5 | 1.413 (5) | C12—H12 | 0.9300 |
| C5—C6 | 1.335 (5) | C13—H13 | 0.9300 |
| C5—H5 | 0.9300 | | |
| | | |
| C1—O1—C4 | 106.9 (3) | O2—C7—C8 | 120.1 (4) |
| C9—O3—H3 | 109.5 | C6—C7—C8 | 120.1 (3) |
| C2—C1—O1 | 110.8 (3) | C13—C8—C9 | 117.1 (4) |
| C2—C1—H1 | 124.6 | C13—C8—C7 | 122.6 (3) |
| O1—C1—H1 | 124.6 | C9—C8—C7 | 120.3 (4) |
| C1—C2—C3 | 106.0 (4) | O3—C9—C10 | 116.6 (4) |
| C1—C2—H2 | 127.0 | O3—C9—C8 | 122.0 (4) |
| C3—C2—H2 | 127.0 | C10—C9—C8 | 121.4 (4) |
| C4—C3—C2 | 108.2 (4) | C11—C10—C9 | 119.2 (4) |
| C4—C3—H3A | 125.9 | C11—C10—H10 | 120.4 |
| C2—C3—H3A | 125.9 | C9—C10—H10 | 120.4 |
| C3—C4—O1 | 108.2 (3) | C10—C11—C12 | 121.6 (4) |
| C3—C4—C5 | 133.3 (4) | C10—C11—H11 | 119.2 |
| O1—C4—C5 | 118.5 (3) | C12—C11—H11 | 119.2 |
| C6—C5—C4 | 125.7 (3) | C13—C12—C11 | 118.8 (4) |
| C6—C5—H5 | 117.1 | C13—C12—H12 | 120.6 |
| C4—C5—H5 | 117.1 | C11—C12—H12 | 120.6 |
| C5—C6—C7 | 121.6 (3) | C12—C13—C8 | 122.0 (4) |
| C5—C6—H6 | 119.2 | C12—C13—H13 | 119.0 |
| C7—C6—H6 | 119.2 | C8—C13—H13 | 119.0 |
| O2—C7—C6 | 119.7 (3) | | |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O2 | 0.82 | 1.84 | 2.544 (4) | 144 |
| C1—H1···O2i | 0.93 | 2.59 | 3.400 (5) | 146 |
| C3—H3A···O3ii | 0.93 | 2.59 | 3.504 (5) | 169 |
| Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+2, y−1/2, −z+3/2. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O2 | 0.82 | 1.84 | 2.544 (4) | 144 |
| C1—H1···O2i | 0.93 | 2.59 | 3.400 (5) | 146 |
| C3—H3A···O3ii | 0.93 | 2.59 | 3.504 (5) | 169 |
| Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+2, y−1/2, −z+3/2. |
This project was supported by the Foundation of Dongchang College, Liaocheng
University (grant No. LG0801).
Li, Z.-D., Huang, L.-Z., Su, G.-B. & Wang, H.-Y. (1992). Chin. J. Struct. Chem. 11, 1–4.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
![[Figure 1]](./cv2448fig1thm.gif)
In continuation of our ongoing program directed to the development of environmentally benign methods of chemical synthesis, we describe in this paper a user-friendly, solvent-free protocol for the synthesis of chalcones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions. Using this method, which can be considered as a a general method for the synthesis of chalcones, we obtained the title compound, (I). We present here its crystal structure.
In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in related compound (Li et al., 1992). The benzene and furan rings form a dihedral angle of 8.35 (7)°. In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into sheets parallel to bc plane.