organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Fraxinellone

aJiangsu Chiatai Tianqing Pharmaceutical Co. Ltd, Nanjing 210042, People's Repulic of China, and, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China
*Correspondence e-mail: benbenshell@yahoo.com.cn

(Received 27 April 2011; accepted 15 May 2011; online 20 May 2011)

In the title compound, C14H16O3 [systematic name: (3R*,3aR*)-3-(3-furan­yl)-3a,7-dimethyl-3a,4,5,6-tetra­hydro-2-benzofuran-1(3H)-one], the pendant methyl and furan groups attached to the stereogenic centres lie to the same side of the fused ring system. The dihedral angle between the five-membered rings is 74.8 (2)°; the fused five-membered ring adopts a twisted conformation. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions, which generate [100] chains.

Related literature

For background to fraxinellone and its biological activity, see: Kim et al. (2009[Kim, J. H., Park, Y. M., Shin, J. S., Park, S. J., Choi, J. H., Jung, H. J., Park, H. J. & Lee, K. T. (2009). Biol. Pharm. Bull. pp. 1062-1068.]); Sun et al. (2009[Sun, Y., Qin, Y., Gong, F. Y., Wu, X. F., Hua, Z. C., Chen, T. & Xu, Q. (2009). Biochem. Pharmacol. pp. 1717-1724.]); Liu et al. (2009[Liu, Z. L., Ho, S. H. & Goh, S. H. (2009). Insect Sci., pp. 147-155.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16O3

  • Mr = 232.27

  • Orthorhombic, P 21 21 21

  • a = 5.940 (3) Å

  • b = 12.661 (6) Å

  • c = 15.921 (7) Å

  • V = 1197.3 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.20 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.982, Tmax = 0.984

  • 10397 measured reflections

  • 1733 independent reflections

  • 1331 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.113

  • S = 1.07

  • 1733 reflections

  • 156 parameters

  • H-atom parameters constrained

  • Δρmax = 0.12 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯O1i 0.98 2.58 3.510 (3) 158
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

There has been much research interest in fraxinellone due to its biological activities (Kim et al. (2009); Sun et al. (2009); Liu et al. (2009)). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The dihedral angle between the C1—C2—C7—C8—O2 and C12—C11—C14—C13—O3 rings is 74.8 (2)°.

Related literature top

For background to fraxinellone and its biological activity, see: Kim et al. (2009); Sun et al. (2009); Liu et al. (2009). For standard bond lengths, see: Allen et al. (1987).

Experimental top

In order to extract the fraxinellone with bioactivity containing in Dictamnus dasycarpus Turks, 100 g/L milk of lime wetting plant material, was extracted by using refluent extract method with petroleum ether as a solvent. The residue was separated with methanol and petroleum ether, and recrystallized in methanol. It was further purified on a silica gel column. Crystals suitable for X-ray structure analysis were obtained by slow evaporation of a solution in methanol at room temperature.

Refinement top

Anomalous dispersion was negligible and Friedel pairs were merged before refinement. All H atoms were positioned geometrically (C—H = 0.93 Å for the aromatic H atoms and C—H = 0.96 Å for the aliphatic H atoms) and were refined as riding, with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.2Ueq(N).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
(3R*,3aR*)-3-(3-furanyl)-3a,4,5,6- tetrahydro-3a,7-dimethyl-2-benzofuran-1(3H)-one top
Crystal data top
C14H16O3F(000) = 496
Mr = 232.27Dx = 1.288 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 5.940 (3) Åθ = 9–12°
b = 12.661 (6) ŵ = 0.09 mm1
c = 15.921 (7) ÅT = 298 K
V = 1197.3 (9) Å3Block, colorless
Z = 40.20 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD
diffractometer
1733 independent reflections
Radiation source: fine-focus sealed tube1331 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ϕ and ω scansθmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 77
Tmin = 0.982, Tmax = 0.984k = 1716
10397 measured reflectionsl = 1921
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0425P)2 + 0.1558P]
where P = (Fo2 + 2Fc2)/3
1733 reflections(Δ/σ)max < 0.001
156 parametersΔρmax = 0.12 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C14H16O3V = 1197.3 (9) Å3
Mr = 232.27Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.940 (3) ŵ = 0.09 mm1
b = 12.661 (6) ÅT = 298 K
c = 15.921 (7) Å0.20 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD
diffractometer
1733 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1331 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.984Rint = 0.049
10397 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.07Δρmax = 0.12 e Å3
1733 reflectionsΔρmin = 0.17 e Å3
156 parameters
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
xyzUiso*/Ueq
O10.5425 (3)0.10394 (15)0.61505 (12)0.0558 (5)
O20.2594 (3)0.00000 (13)0.65310 (9)0.0423 (4)
O30.2584 (5)0.24662 (18)0.72681 (14)0.0806 (8)
C10.3749 (4)0.05682 (18)0.59460 (15)0.0391 (5)
C20.2628 (4)0.04409 (17)0.51292 (14)0.0377 (5)
C30.2806 (5)0.10573 (18)0.44505 (15)0.0428 (6)
C40.1270 (5)0.0894 (2)0.37091 (17)0.0571 (7)
H4A0.03340.15170.36490.069*
H4B0.21900.08400.32080.069*
C50.0254 (5)0.0067 (2)0.37495 (17)0.0583 (7)
H5A0.15720.00580.34040.070*
H5B0.05390.06710.35200.070*
C60.1009 (4)0.0323 (2)0.46465 (16)0.0488 (6)
H6A0.19160.09600.46450.059*
H6B0.19250.02510.48620.059*
C70.1041 (4)0.04793 (17)0.52105 (13)0.0355 (5)
C80.0486 (4)0.03908 (17)0.61578 (14)0.0364 (5)
H80.06670.01560.62280.044*
C90.4404 (5)0.1978 (2)0.4381 (2)0.0599 (8)
H9A0.55890.18060.39950.090*
H9B0.36030.25870.41810.090*
H9C0.50370.21270.49230.090*
C100.2300 (5)0.15067 (19)0.50129 (15)0.0466 (6)
H10A0.35770.15720.53790.070*
H10B0.13110.20970.50960.070*
H10C0.28020.14950.44400.070*
C110.0265 (4)0.13529 (19)0.66193 (14)0.0416 (6)
C120.2403 (6)0.1508 (2)0.68932 (16)0.0563 (7)
H120.35740.10260.68330.068*
C130.0487 (6)0.2921 (2)0.72441 (18)0.0579 (8)
H130.01160.35770.74670.069*
C140.0930 (6)0.2275 (2)0.68509 (17)0.0542 (7)
H140.24450.24060.67460.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0482 (11)0.0579 (10)0.0612 (11)0.0135 (10)0.0039 (10)0.0022 (9)
O20.0457 (9)0.0438 (8)0.0372 (8)0.0068 (8)0.0002 (8)0.0015 (7)
O30.101 (2)0.0835 (16)0.0576 (12)0.0376 (17)0.0124 (14)0.0099 (11)
C10.0405 (13)0.0328 (11)0.0441 (13)0.0013 (11)0.0046 (11)0.0044 (10)
C20.0383 (13)0.0356 (11)0.0391 (12)0.0052 (11)0.0047 (11)0.0025 (9)
C30.0415 (14)0.0389 (12)0.0480 (14)0.0062 (11)0.0090 (12)0.0047 (10)
C40.0623 (18)0.0652 (16)0.0438 (15)0.0026 (16)0.0025 (14)0.0105 (13)
C50.0666 (19)0.0645 (16)0.0438 (14)0.0014 (16)0.0078 (14)0.0009 (13)
C60.0476 (15)0.0539 (15)0.0449 (14)0.0050 (13)0.0071 (12)0.0008 (12)
C70.0375 (12)0.0348 (11)0.0342 (11)0.0006 (10)0.0034 (10)0.0013 (9)
C80.0351 (12)0.0373 (11)0.0369 (11)0.0000 (10)0.0024 (10)0.0023 (9)
C90.0583 (19)0.0508 (15)0.0708 (19)0.0022 (15)0.0055 (16)0.0183 (14)
C100.0561 (16)0.0385 (11)0.0451 (13)0.0066 (13)0.0066 (14)0.0048 (10)
C110.0467 (15)0.0454 (13)0.0326 (11)0.0058 (12)0.0009 (11)0.0024 (10)
C120.0607 (18)0.0642 (16)0.0439 (14)0.0099 (16)0.0075 (16)0.0036 (13)
C130.082 (2)0.0455 (14)0.0465 (15)0.0112 (16)0.0031 (16)0.0107 (12)
C140.0634 (19)0.0508 (14)0.0485 (15)0.0008 (15)0.0041 (15)0.0052 (12)
Geometric parameters (Å, º) top
O1—C11.205 (3)C6—H6B0.9700
O2—C11.362 (3)C7—C101.533 (3)
O2—C81.471 (3)C7—C81.548 (3)
O3—C121.357 (3)C8—C111.491 (3)
O3—C131.373 (4)C8—H80.9800
C1—C21.470 (3)C9—H9A0.9600
C2—C31.337 (3)C9—H9B0.9600
C2—C71.504 (3)C9—H9C0.9600
C3—C41.506 (4)C10—H10A0.9600
C3—C91.507 (4)C10—H10B0.9600
C4—C51.518 (4)C10—H10C0.9600
C4—H4A0.9700C11—C121.357 (4)
C4—H4B0.9700C11—C141.415 (4)
C5—C61.531 (4)C12—H120.9300
C5—H5A0.9700C13—C141.331 (4)
C5—H5B0.9700C13—H130.9300
C6—C71.526 (3)C14—H140.9300
C6—H6A0.9700
C1—O2—C8109.29 (17)C6—C7—C8113.2 (2)
C12—O3—C13106.9 (3)C10—C7—C8111.41 (18)
O1—C1—O2119.5 (2)O2—C8—C11109.30 (19)
O1—C1—C2131.9 (2)O2—C8—C7103.70 (17)
O2—C1—C2108.6 (2)C11—C8—C7119.00 (18)
C3—C2—C1128.0 (2)O2—C8—H8108.1
C3—C2—C7124.8 (2)C11—C8—H8108.1
C1—C2—C7107.02 (18)C7—C8—H8108.1
C2—C3—C4120.4 (2)C3—C9—H9A109.5
C2—C3—C9124.1 (3)C3—C9—H9B109.5
C4—C3—C9115.5 (2)H9A—C9—H9B109.5
C3—C4—C5116.0 (2)C3—C9—H9C109.5
C3—C4—H4A108.3H9A—C9—H9C109.5
C5—C4—H4A108.3H9B—C9—H9C109.5
C3—C4—H4B108.3C7—C10—H10A109.5
C5—C4—H4B108.3C7—C10—H10B109.5
H4A—C4—H4B107.4H10A—C10—H10B109.5
C4—C5—C6112.6 (2)C7—C10—H10C109.5
C4—C5—H5A109.1H10A—C10—H10C109.5
C6—C5—H5A109.1H10B—C10—H10C109.5
C4—C5—H5B109.1C12—C11—C14105.5 (2)
C6—C5—H5B109.1C12—C11—C8123.8 (3)
H5A—C5—H5B107.8C14—C11—C8130.7 (2)
C7—C6—C5110.0 (2)C11—C12—O3110.2 (3)
C7—C6—H6A109.7C11—C12—H12124.9
C5—C6—H6A109.7O3—C12—H12124.9
C7—C6—H6B109.7C14—C13—O3109.2 (2)
C5—C6—H6B109.7C14—C13—H13125.4
H6A—C6—H6B108.2O3—C13—H13125.4
C2—C7—C6110.41 (19)C13—C14—C11108.2 (3)
C2—C7—C10109.49 (19)C13—C14—H14125.9
C6—C7—C10112.3 (2)C11—C14—H14125.9
C2—C7—C899.28 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O1i0.982.583.510 (3)158
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC14H16O3
Mr232.27
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)5.940 (3), 12.661 (6), 15.921 (7)
V3)1197.3 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.20 × 0.18
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.982, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
10397, 1733, 1331
Rint0.049
(sin θ/λ)max1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.113, 1.07
No. of reflections1733
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.12, 0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O1i0.982.583.510 (3)158
Symmetry code: (i) x1, y, z.
 

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKim, J. H., Park, Y. M., Shin, J. S., Park, S. J., Choi, J. H., Jung, H. J., Park, H. J. & Lee, K. T. (2009). Biol. Pharm. Bull. pp. 1062–1068.  CrossRef Google Scholar
First citationLiu, Z. L., Ho, S. H. & Goh, S. H. (2009). Insect Sci., pp. 147–155.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, Y., Qin, Y., Gong, F. Y., Wu, X. F., Hua, Z. C., Chen, T. & Xu, Q. (2009). Biochem. Pharmacol. pp. 1717–1724.  CrossRef Google Scholar

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