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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2161.
Published online 2008 October 22. doi:  10.1107/S1600536808031644
PMCID: PMC2959741

(E)-3-(2-Fur­yl)-1-(2-hydroxy­phen­yl)prop-2-en-1-one

Abstract

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—H(...)O hydrogen bonds link mol­ecules into sheets parallel to the bc plane.

Related literature

For a related crystal structure, see: Li et al. (1992 [triangle]).

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Object name is e-64-o2161-scheme1.jpg

Experimental

Crystal data

  • C13H10O3
  • M r = 214.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2161-efi1.jpg
  • a = 3.8560 (5) Å
  • b = 15.6565 (14) Å
  • c = 17.309 (2) Å
  • β = 95.065 (2)°
  • V = 1040.9 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.27 × 0.25 × 0.07 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.974, T max = 0.993
  • 5153 measured reflections
  • 1848 independent reflections
  • 668 reflections with I > 2σ(I)
  • R int = 0.126

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.184
  • S = 0.81
  • 1848 reflections
  • 146 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031644/cv2448sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031644/cv2448Isup2.hkl

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

Acknowledgments

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

supplementary crystallographic information

Comment

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.

Experimental

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%.

Refinement

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).

Figures

Fig. 1.
The molecular structure of (I) showing the atomic numbering and 40% probability displacement ellipsoids.

Crystal data

C13H10O3F(000) = 448
Mr = 214.21Dx = 1.367 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 3.8560 (5) ÅCell parameters from 438 reflections
b = 15.6565 (14) Åθ = 2.4–18.4°
c = 17.309 (2) ŵ = 0.10 mm1
β = 95.065 (2)°T = 298 K
V = 1040.9 (2) Å3Block, colourless
Z = 40.27 × 0.25 × 0.07 mm

Data collection

Siemens SMART CCD area-detector diffractometer1848 independent reflections
Radiation source: fine-focus sealed tube668 reflections with I > 2σ(I)
graphiteRint = 0.126
Detector resolution: [var phi] and ω pixels mm-1θmax = 25.0°, θmin = 1.8°
[var phi] and ω scansh = −4→4
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −7→18
Tmin = 0.974, Tmax = 0.993l = −20→20
5153 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 0.81w = 1/[σ2(Fo2) + (0.0721P)2] where P = (Fo2 + 2Fc2)/3
1848 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = −0.19 e Å3

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
O11.0561 (7)0.73465 (16)0.48262 (15)0.0794 (9)
O20.8017 (8)0.83794 (18)0.74522 (15)0.0885 (11)
O30.5477 (10)0.9672 (2)0.80912 (17)0.1030 (12)
H30.65460.92200.80870.154*
C11.1454 (12)0.6735 (3)0.4327 (2)0.0842 (15)
H11.14720.68110.37940.101*
C21.2297 (11)0.6018 (3)0.4699 (3)0.0769 (13)
H21.30180.55100.44850.092*
C31.1887 (11)0.6177 (3)0.5478 (2)0.0748 (13)
H3A1.22710.57880.58820.090*
C41.0842 (10)0.6991 (2)0.5544 (2)0.0584 (10)
C50.9983 (9)0.7493 (2)0.6177 (2)0.0608 (11)
H51.02220.72400.66650.073*
C60.8860 (10)0.8300 (2)0.6137 (2)0.0598 (11)
H60.86760.85780.56610.072*
C70.7918 (10)0.8754 (2)0.6822 (2)0.0600 (11)
C80.6700 (9)0.9648 (2)0.6757 (2)0.0553 (10)
C90.5559 (11)1.0064 (3)0.7399 (2)0.0690 (12)
C100.4467 (12)1.0901 (3)0.7358 (3)0.0835 (14)
H100.36971.11700.77900.100*
C110.4529 (13)1.1329 (3)0.6679 (3)0.0930 (16)
H110.37691.18930.66490.112*
C120.5685 (12)1.0951 (3)0.6033 (3)0.0839 (14)
H120.57471.12560.55730.101*
C130.6745 (11)1.0117 (3)0.6079 (2)0.0702 (12)
H130.75180.98580.56420.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.111 (3)0.0632 (19)0.0648 (18)0.0106 (16)0.0132 (16)−0.0022 (16)
O20.138 (3)0.067 (2)0.0625 (18)0.0095 (18)0.0190 (18)0.0029 (15)
O30.150 (4)0.087 (3)0.076 (2)0.010 (2)0.033 (2)−0.0105 (18)
C10.112 (4)0.076 (3)0.065 (3)0.008 (3)0.015 (3)−0.014 (3)
C20.080 (4)0.057 (3)0.095 (3)0.008 (2)0.012 (3)−0.016 (3)
C30.086 (4)0.061 (3)0.078 (3)0.008 (2)0.011 (2)−0.004 (2)
C40.065 (3)0.053 (2)0.058 (2)−0.002 (2)0.010 (2)−0.001 (2)
C50.063 (3)0.059 (2)0.061 (2)0.001 (2)0.010 (2)0.004 (2)
C60.067 (3)0.058 (2)0.054 (2)0.002 (2)0.005 (2)−0.003 (2)
C70.064 (3)0.057 (3)0.059 (2)−0.005 (2)0.004 (2)0.001 (2)
C80.055 (3)0.053 (2)0.058 (2)−0.0020 (19)0.006 (2)−0.001 (2)
C90.071 (3)0.069 (3)0.068 (3)−0.001 (2)0.009 (2)−0.009 (2)
C100.080 (4)0.073 (3)0.095 (4)0.008 (3)0.001 (3)−0.023 (3)
C110.093 (4)0.061 (3)0.122 (4)0.014 (3)−0.014 (3)−0.013 (3)
C120.099 (4)0.063 (3)0.086 (3)0.000 (3)−0.008 (3)0.007 (3)
C130.078 (3)0.056 (3)0.076 (3)−0.004 (2)0.007 (2)−0.005 (2)

Geometric parameters (Å, °)

O1—C11.354 (4)C6—C71.455 (5)
O1—C41.357 (4)C6—H60.9300
O2—C71.237 (4)C7—C81.476 (5)
O3—C91.349 (4)C8—C131.386 (5)
O3—H30.8200C8—C91.393 (5)
C1—C21.321 (5)C9—C101.377 (6)
C1—H10.9300C10—C111.354 (5)
C2—C31.394 (5)C10—H100.9300
C2—H20.9300C11—C121.374 (6)
C3—C41.343 (5)C11—H110.9300
C3—H3A0.9300C12—C131.368 (5)
C4—C51.413 (5)C12—H120.9300
C5—C61.335 (5)C13—H130.9300
C5—H50.9300
C1—O1—C4106.9 (3)O2—C7—C8120.1 (4)
C9—O3—H3109.5C6—C7—C8120.1 (3)
C2—C1—O1110.8 (3)C13—C8—C9117.1 (4)
C2—C1—H1124.6C13—C8—C7122.6 (3)
O1—C1—H1124.6C9—C8—C7120.3 (4)
C1—C2—C3106.0 (4)O3—C9—C10116.6 (4)
C1—C2—H2127.0O3—C9—C8122.0 (4)
C3—C2—H2127.0C10—C9—C8121.4 (4)
C4—C3—C2108.2 (4)C11—C10—C9119.2 (4)
C4—C3—H3A125.9C11—C10—H10120.4
C2—C3—H3A125.9C9—C10—H10120.4
C3—C4—O1108.2 (3)C10—C11—C12121.6 (4)
C3—C4—C5133.3 (4)C10—C11—H11119.2
O1—C4—C5118.5 (3)C12—C11—H11119.2
C6—C5—C4125.7 (3)C13—C12—C11118.8 (4)
C6—C5—H5117.1C13—C12—H12120.6
C4—C5—H5117.1C11—C12—H12120.6
C5—C6—C7121.6 (3)C12—C13—C8122.0 (4)
C5—C6—H6119.2C12—C13—H13119.0
C7—C6—H6119.2C8—C13—H13119.0
O2—C7—C6119.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.842.544 (4)144
C1—H1···O2i0.932.593.400 (5)146
C3—H3A···O3ii0.932.593.504 (5)169

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2448).

References

  • 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. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography