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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3085.
Published online 2009 November 14. doi:  10.1107/S160053680904728X
PMCID: PMC2972156

(2E,6E)-2,6-Difurfurylidenecyclo­hexa­none

Abstract

The complete mol­ecule of the title compound, C16H14O3, is generated by crystallographic mirror symmetry, with two C atoms and one O atom lying on the mirror plane. The mol­ecule adopts an E configuration about the C=C bond and the dihedral angle between the furan rings is 16.1 (2)°.

Related literature

For general background to the use of bis­(aryl­methyl­idene)cyclo­alkanones as building blocks for the synthesis of biologically active heterocycles, see: Guilford et al. (1999 [triangle]). For related structures, see: Liu & Chen (2009 [triangle]); Liu (2009 [triangle]); Shi et al. (2008 [triangle]).

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Object name is e-65-o3085-scheme1.jpg

Experimental

Crystal data

  • C16H14O3
  • M r = 254.27
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3085-efi1.jpg
  • a = 7.7313 (11) Å
  • b = 15.658 (2) Å
  • c = 10.3388 (14) Å
  • V = 1251.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.15 × 0.10 × 0.06 mm

Data collection

  • Siemens SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.986, T max = 0.995
  • 6025 measured reflections
  • 1158 independent reflections
  • 731 reflections with I > 2σ(I)
  • R int = 0.072

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.122
  • S = 1.03
  • 1158 reflections
  • 92 parameters
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.16 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904728X/hb5212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904728X/hb5212Isup2.hkl

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

Acknowledgments

This project was supported by the Postgraduate Foundation of Taishan University (No.Y07–2-14).

supplementary crystallographic information

Comment

Bis(arylmethylidene)cycloalkanones are widely used as building blocks for the synthesis of biologically active heterocycles (Guilford et al., 1999). In the present paper, we describe the crystal stucture of the title compound. The molecule posseses normal geometric parameters and adopts an E-configuration about the central olefinic bonds (Fig. 1). The cyclohexanone ring and the furan rings are alomst coplanar which allows conjugation. Similar structures have been observed in the related substituted cyclopentanone and cyclohexanone analogues reported by Liu & Chen (2009); Liu (2009); Shi et al. (2008).

Experimental

Tetrabutylammonium bromide (0.5 mmol) and NaOH (10 mmol) were dissolved in the mixture of water (10 ml) and ethanol (4 ml). The solution was stirred at room temperature for 10 min, followed by dropwise addition of a mixture of furaldehyde (20 mmol) and cyclohexanone (10 mmol).The mixture was stirred at the temperature of 303 K for 2 h. When the reaction was complete, the residue was filtered. The precipitate was washed by water and recrystallized from ethyl acetate to yield yellow blocks of (I). Analysis calculated for C16H14O3: C 75.59, H 5.51%; found: C 75.65, H 5.46%.

Refinement

All H-atoms were initially located in a difference Fourier map and were placed in geometrically idealized positions, with C—H = 0.93 - 0.97 Å and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. Atoms with the suffix A are generated by (x, 3/2–y, z).

Crystal data

C16H14O3Dx = 1.349 Mg m3
Mr = 254.27Melting point: 417 K
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 472 reflections
a = 7.7313 (11) Åθ = 2.6–19.2°
b = 15.658 (2) ŵ = 0.09 mm1
c = 10.3388 (14) ÅT = 295 K
V = 1251.5 (3) Å3Block, yellow
Z = 40.15 × 0.10 × 0.06 mm
F(000) = 536

Data collection

Siemens SMART CCD diffractometer1158 independent reflections
Radiation source: fine-focus sealed tube731 reflections with I > 2σ(I)
graphiteRint = 0.072
ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.986, Tmax = 0.995k = −15→18
6025 measured reflectionsl = −12→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.122w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2592P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1158 reflectionsΔρmax = 0.17 e Å3
92 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (2)

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
O10.0245 (3)0.75000.0550 (2)0.0606 (7)
O20.1187 (2)0.44953 (11)0.12636 (15)0.0689 (6)
C10.0568 (4)0.75000.1720 (3)0.0461 (8)
C20.0806 (3)0.66875 (14)0.24340 (19)0.0434 (6)
C30.0950 (3)0.67029 (14)0.3886 (2)0.0509 (7)
H3A0.21600.66680.41290.061*
H3B0.03670.62060.42390.061*
C40.0172 (4)0.75000.4467 (3)0.0527 (9)
H4A0.03660.75000.53940.063*
H4B−0.10670.75000.43190.063*
C50.0954 (3)0.59655 (14)0.1739 (2)0.0494 (6)
H50.07940.60220.08520.059*
C60.1324 (3)0.51243 (15)0.2189 (2)0.0497 (7)
C70.1845 (4)0.47563 (15)0.3310 (2)0.0602 (7)
H70.20480.50360.40890.072*
C80.2024 (4)0.38729 (16)0.3081 (2)0.0646 (8)
H80.23660.34600.36740.078*
C90.1606 (4)0.37468 (17)0.1841 (3)0.0729 (9)
H90.16030.32180.14320.087*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0879 (19)0.0532 (15)0.0406 (13)0.000−0.0145 (12)0.000
O20.1102 (16)0.0485 (11)0.0481 (10)0.0097 (10)0.0021 (10)−0.0052 (8)
C10.051 (2)0.051 (2)0.0365 (17)0.000−0.0044 (15)0.000
C20.0445 (14)0.0456 (14)0.0402 (12)−0.0018 (11)−0.0005 (10)−0.0007 (11)
C30.0656 (17)0.0479 (14)0.0391 (12)−0.0026 (13)−0.0014 (11)0.0010 (11)
C40.061 (2)0.059 (2)0.0387 (17)0.0000.0036 (16)0.000
C50.0538 (15)0.0524 (16)0.0421 (13)−0.0002 (12)−0.0027 (11)0.0021 (11)
C60.0596 (17)0.0451 (14)0.0445 (13)−0.0001 (12)0.0003 (11)−0.0024 (11)
C70.0767 (19)0.0525 (16)0.0513 (14)−0.0008 (14)−0.0073 (13)−0.0004 (12)
C80.081 (2)0.0479 (16)0.0650 (17)0.0033 (14)0.0018 (15)0.0110 (13)
C90.109 (2)0.0432 (16)0.0669 (18)0.0100 (16)0.0138 (17)0.0018 (14)

Geometric parameters (Å, °)

O1—C11.235 (3)C4—H4A0.9700
O2—C91.355 (3)C4—H4B0.9700
O2—C61.377 (2)C5—C61.426 (3)
C1—C2i1.482 (3)C5—H50.9300
C1—C21.482 (3)C6—C71.355 (3)
C2—C51.344 (3)C7—C81.410 (3)
C2—C31.506 (3)C7—H70.9300
C3—C41.510 (3)C8—C91.336 (3)
C3—H3A0.9700C8—H80.9300
C3—H3B0.9700C9—H90.9300
C4—C3i1.510 (3)
C9—O2—C6107.08 (19)C3i—C4—H4B109.3
O1—C1—C2i120.85 (13)H4A—C4—H4B108.0
O1—C1—C2120.85 (13)C2—C5—C6128.3 (2)
C2i—C1—C2118.2 (3)C2—C5—H5115.9
C5—C2—C1117.8 (2)C6—C5—H5115.9
C5—C2—C3122.7 (2)C7—C6—O2108.2 (2)
C1—C2—C3119.5 (2)C7—C6—C5137.0 (2)
C2—C3—C4112.3 (2)O2—C6—C5114.73 (19)
C2—C3—H3A109.1C6—C7—C8107.6 (2)
C4—C3—H3A109.1C6—C7—H7126.2
C2—C3—H3B109.1C8—C7—H7126.2
C4—C3—H3B109.1C9—C8—C7106.4 (2)
H3A—C3—H3B107.9C9—C8—H8126.8
C3—C4—C3i111.5 (3)C7—C8—H8126.8
C3—C4—H4A109.3C8—C9—O2110.7 (2)
C3i—C4—H4A109.3C8—C9—H9124.7
C3—C4—H4B109.3O2—C9—H9124.7
O1—C1—C2—C511.1 (4)C9—O2—C6—C70.9 (3)
C2i—C1—C2—C5−166.16 (18)C9—O2—C6—C5179.0 (2)
O1—C1—C2—C3−171.5 (3)C2—C5—C6—C7−10.1 (5)
C2i—C1—C2—C311.2 (4)C2—C5—C6—O2172.5 (2)
C5—C2—C3—C4−161.0 (2)O2—C6—C7—C8−0.5 (3)
C1—C2—C3—C421.8 (3)C5—C6—C7—C8−178.0 (3)
C2—C3—C4—C3i−55.1 (3)C6—C7—C8—C90.0 (3)
C1—C2—C5—C6174.6 (2)C7—C8—C9—O20.6 (3)
C3—C2—C5—C6−2.7 (4)C6—O2—C9—C8−0.9 (3)

Symmetry codes: (i) x, −y+3/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5212).

References

  • Guilford, W. J., Shaw, K. J., Dallas, J. L., Koovakkat, S., Lee, W., Liang, A., Light, D. R., McCarrick, M. A., Whitlow, M., Ye, B. & Morrissey, M. M. (1999). J. Med. Chem. 42, 5415–5425. [PubMed]
  • Liu, D. (2009). Acta Cryst. E65, o694. [PMC free article] [PubMed]
  • Liu, D. & Chen, G. (2009). Acta Cryst. E65, o928. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shi, X., Li, S. & Liu, Z. (2008). Acta Cryst. E64, o2199. [PMC free article] [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