organic compounds
(2E,6E)-2,6-Difurfurylidenecyclohexanone
aDepartment of Chemistry and Environmental Science, Taishan University, 271021 Taian, Shandong, People's Republic of China
*Correspondence e-mail: mashy910@163.com
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). For related structures, see: Liu & Chen (2009); Liu (2009); Shi et al. (2008).
Experimental
Crystal data
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Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996); data reduction: SAINT; 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.
Supporting information
10.1107/S160053680904728X/hb5212sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680904728X/hb5212Isup2.hkl
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%.
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).
Data collection: SMART (Siemens, 1996); cell
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).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). |
C16H14O3 | Dx = 1.349 Mg m−3 |
Mr = 254.27 | Melting point: 417 K |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 472 reflections |
a = 7.7313 (11) Å | θ = 2.6–19.2° |
b = 15.658 (2) Å | µ = 0.09 mm−1 |
c = 10.3388 (14) Å | T = 295 K |
V = 1251.5 (3) Å3 | Block, yellow |
Z = 4 | 0.15 × 0.10 × 0.06 mm |
F(000) = 536 |
Siemens SMART CCD diffractometer | 1158 independent reflections |
Radiation source: fine-focus sealed tube | 731 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
ω scans | θmax = 25.1°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.986, Tmax = 0.995 | k = −15→18 |
6025 measured reflections | l = −12→9 |
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)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2592P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1158 reflections | Δρmax = 0.17 e Å−3 |
92 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.017 (2) |
C16H14O3 | V = 1251.5 (3) Å3 |
Mr = 254.27 | Z = 4 |
Orthorhombic, Pnma | Mo Kα radiation |
a = 7.7313 (11) Å | µ = 0.09 mm−1 |
b = 15.658 (2) Å | T = 295 K |
c = 10.3388 (14) Å | 0.15 × 0.10 × 0.06 mm |
Siemens SMART CCD diffractometer | 1158 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 731 reflections with I > 2σ(I) |
Tmin = 0.986, Tmax = 0.995 | Rint = 0.072 |
6025 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.17 e Å−3 |
1158 reflections | Δρmin = −0.16 e Å−3 |
92 parameters |
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 | 0.0245 (3) | 0.7500 | 0.0550 (2) | 0.0606 (7) | |
O2 | 0.1187 (2) | 0.44953 (11) | 0.12636 (15) | 0.0689 (6) | |
C1 | 0.0568 (4) | 0.7500 | 0.1720 (3) | 0.0461 (8) | |
C2 | 0.0806 (3) | 0.66875 (14) | 0.24340 (19) | 0.0434 (6) | |
C3 | 0.0950 (3) | 0.67029 (14) | 0.3886 (2) | 0.0509 (7) | |
H3A | 0.2160 | 0.6668 | 0.4129 | 0.061* | |
H3B | 0.0367 | 0.6206 | 0.4239 | 0.061* | |
C4 | 0.0172 (4) | 0.7500 | 0.4467 (3) | 0.0527 (9) | |
H4A | 0.0366 | 0.7500 | 0.5394 | 0.063* | |
H4B | −0.1067 | 0.7500 | 0.4319 | 0.063* | |
C5 | 0.0954 (3) | 0.59655 (14) | 0.1739 (2) | 0.0494 (6) | |
H5 | 0.0794 | 0.6022 | 0.0852 | 0.059* | |
C6 | 0.1324 (3) | 0.51243 (15) | 0.2189 (2) | 0.0497 (7) | |
C7 | 0.1845 (4) | 0.47563 (15) | 0.3310 (2) | 0.0602 (7) | |
H7 | 0.2048 | 0.5036 | 0.4089 | 0.072* | |
C8 | 0.2024 (4) | 0.38729 (16) | 0.3081 (2) | 0.0646 (8) | |
H8 | 0.2366 | 0.3460 | 0.3674 | 0.078* | |
C9 | 0.1606 (4) | 0.37468 (17) | 0.1841 (3) | 0.0729 (9) | |
H9 | 0.1603 | 0.3218 | 0.1432 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0879 (19) | 0.0532 (15) | 0.0406 (13) | 0.000 | −0.0145 (12) | 0.000 |
O2 | 0.1102 (16) | 0.0485 (11) | 0.0481 (10) | 0.0097 (10) | 0.0021 (10) | −0.0052 (8) |
C1 | 0.051 (2) | 0.051 (2) | 0.0365 (17) | 0.000 | −0.0044 (15) | 0.000 |
C2 | 0.0445 (14) | 0.0456 (14) | 0.0402 (12) | −0.0018 (11) | −0.0005 (10) | −0.0007 (11) |
C3 | 0.0656 (17) | 0.0479 (14) | 0.0391 (12) | −0.0026 (13) | −0.0014 (11) | 0.0010 (11) |
C4 | 0.061 (2) | 0.059 (2) | 0.0387 (17) | 0.000 | 0.0036 (16) | 0.000 |
C5 | 0.0538 (15) | 0.0524 (16) | 0.0421 (13) | −0.0002 (12) | −0.0027 (11) | 0.0021 (11) |
C6 | 0.0596 (17) | 0.0451 (14) | 0.0445 (13) | −0.0001 (12) | 0.0003 (11) | −0.0024 (11) |
C7 | 0.0767 (19) | 0.0525 (16) | 0.0513 (14) | −0.0008 (14) | −0.0073 (13) | −0.0004 (12) |
C8 | 0.081 (2) | 0.0479 (16) | 0.0650 (17) | 0.0033 (14) | 0.0018 (15) | 0.0110 (13) |
C9 | 0.109 (2) | 0.0432 (16) | 0.0669 (18) | 0.0100 (16) | 0.0138 (17) | 0.0018 (14) |
O1—C1 | 1.235 (3) | C4—H4A | 0.9700 |
O2—C9 | 1.355 (3) | C4—H4B | 0.9700 |
O2—C6 | 1.377 (2) | C5—C6 | 1.426 (3) |
C1—C2i | 1.482 (3) | C5—H5 | 0.9300 |
C1—C2 | 1.482 (3) | C6—C7 | 1.355 (3) |
C2—C5 | 1.344 (3) | C7—C8 | 1.410 (3) |
C2—C3 | 1.506 (3) | C7—H7 | 0.9300 |
C3—C4 | 1.510 (3) | C8—C9 | 1.336 (3) |
C3—H3A | 0.9700 | C8—H8 | 0.9300 |
C3—H3B | 0.9700 | C9—H9 | 0.9300 |
C4—C3i | 1.510 (3) | ||
C9—O2—C6 | 107.08 (19) | C3i—C4—H4B | 109.3 |
O1—C1—C2i | 120.85 (13) | H4A—C4—H4B | 108.0 |
O1—C1—C2 | 120.85 (13) | C2—C5—C6 | 128.3 (2) |
C2i—C1—C2 | 118.2 (3) | C2—C5—H5 | 115.9 |
C5—C2—C1 | 117.8 (2) | C6—C5—H5 | 115.9 |
C5—C2—C3 | 122.7 (2) | C7—C6—O2 | 108.2 (2) |
C1—C2—C3 | 119.5 (2) | C7—C6—C5 | 137.0 (2) |
C2—C3—C4 | 112.3 (2) | O2—C6—C5 | 114.73 (19) |
C2—C3—H3A | 109.1 | C6—C7—C8 | 107.6 (2) |
C4—C3—H3A | 109.1 | C6—C7—H7 | 126.2 |
C2—C3—H3B | 109.1 | C8—C7—H7 | 126.2 |
C4—C3—H3B | 109.1 | C9—C8—C7 | 106.4 (2) |
H3A—C3—H3B | 107.9 | C9—C8—H8 | 126.8 |
C3—C4—C3i | 111.5 (3) | C7—C8—H8 | 126.8 |
C3—C4—H4A | 109.3 | C8—C9—O2 | 110.7 (2) |
C3i—C4—H4A | 109.3 | C8—C9—H9 | 124.7 |
C3—C4—H4B | 109.3 | O2—C9—H9 | 124.7 |
O1—C1—C2—C5 | 11.1 (4) | C9—O2—C6—C7 | 0.9 (3) |
C2i—C1—C2—C5 | −166.16 (18) | C9—O2—C6—C5 | 179.0 (2) |
O1—C1—C2—C3 | −171.5 (3) | C2—C5—C6—C7 | −10.1 (5) |
C2i—C1—C2—C3 | 11.2 (4) | C2—C5—C6—O2 | 172.5 (2) |
C5—C2—C3—C4 | −161.0 (2) | O2—C6—C7—C8 | −0.5 (3) |
C1—C2—C3—C4 | 21.8 (3) | C5—C6—C7—C8 | −178.0 (3) |
C2—C3—C4—C3i | −55.1 (3) | C6—C7—C8—C9 | 0.0 (3) |
C1—C2—C5—C6 | 174.6 (2) | C7—C8—C9—O2 | 0.6 (3) |
C3—C2—C5—C6 | −2.7 (4) | C6—O2—C9—C8 | −0.9 (3) |
Symmetry code: (i) x, −y+3/2, z. |
Experimental details
Crystal data | |
Chemical formula | C16H14O3 |
Mr | 254.27 |
Crystal system, space group | Orthorhombic, Pnma |
Temperature (K) | 295 |
a, b, c (Å) | 7.7313 (11), 15.658 (2), 10.3388 (14) |
V (Å3) | 1251.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.15 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Siemens SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.986, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6025, 1158, 731 |
Rint | 0.072 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.122, 1.03 |
No. of reflections | 1158 |
No. of parameters | 92 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This project was supported by the Postgraduate Foundation of Taishan University (No.Y07–2-14).
References
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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).