Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2949
https://doi.org/10.1107/S1600536812038470

(2S*,3S*,3aS*,6S*,7aR*)-3-Hy­dr­oxy-2-[(2R*,3S*)-3-iso­propyl­oxiran-2-yl]-3,6-di­methyl-3,3a,5,6,7,7a-hexa­hydro-1-benzo­furan-4(2H)-one

Mingruo Ding,a Qiaoyin Zhang,a Lei Chen,a Nianyu Huanga and Junzhi Wanga*

aHubei Key Laboratory of Natural Products Research and Development, College of Chemistry and Life Sciences, China Three Gorges University, Yichang, Hubei 443002, People's Republic of China
*Correspondence e-mail: horsedog@163.com

(Received 31 August 2012; accepted 7 September 2012; online 19 September 2012)

In the title compound, C15H24O4, the six-membered ring shows a distorted chair conformation and the five-membered ring adopts an envelope conformation with the C atom bearing the methyl and OH groups as the flap. In the crystal, O—H⋯O hydrogen bonds link the mol­ecules into chains running along the a-axis direction.

Related literature

The title compound was synthesized as a potential gastric cytoprotective agent. For background to gastric diseases, see: Palmer et al. (2010[Palmer, A. M., Chiesa, V., Schmid, A., Muench, G., Grobbel, B., Zimmermann, P. J., Brehm, C., Buhr, W., Simon, W.-A., Kromer, W., Postius, S., Volz, J. & Hess, D. (2010). J. Med. Chem. 53, 3645-3674.]). For pharmacological uses of bis­abol­an­gelone, a sesquiterpene isolated from the roots of Angelica polymorpha Maxim, see: Fang & Liao (2006[Fang, Z. & Liao, Z. (2006). The Medicinal Plants from Enshi of Hubei. Wuhan, China: The Science and Technological Press of Hubei.]); Muckensturm et al. (1981[Muckensturm, B., Duplay, D., Robert, P. C., Simonis, M. T. & Kienlen, J. C. (1981). Biochem. Syst. Ecol. 2, 289-292.]). Huang et al. (2012[Huang, N. Y., Chen, L., Liao, Z. J., Fang, H. B., Wang, J. Z. & Zou, K. (2012). Chin. J. Chem. 30, 71-76.]); Wang et al. (2009[Wang, J. Z., Zhu, L. B., Zou, K., Cheng, F., Dan, F. J., Guo, Z. Y., Cai, Z. J. & Yang, J. (2009). J. Ethnopharma. 123, 343-346.]). For the crystal structure of bis­abolangelone, see: Wang et al. (2007[Wang, J.-Z., Zou, K., Cheng, F. & Dan, F.-J. (2007). Acta Cryst. E63, o2706.]).

[Scheme 1]

Experimental

Crystal data

  • C15H24O4

  • Mr = 268.34

  • Orthorhombic, P 21 21 21

  • a = 6.616 (7) Å

  • b = 9.261 (9) Å

  • c = 25.12 (3) Å

  • V = 1539 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.35 × 0.28 × 0.26 mm
Data collection

  • Rigaku Mercury 375R CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2011[Rigaku (2011). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.972, Tmax = 0.980

  • 16467 measured reflections

  • 2058 independent reflections

  • 1568 reflections with I > 2σ(I)

  • Rint = 0.176
Refinement

  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.185

  • S = 1.03

  • 2058 reflections

  • 177 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3A⋯O4i 0.82 2.02 2.827 (4) 166
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2011[Rigaku (2011). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812038470/bt6831sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038470/bt6831Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038470/bt6831Isup3.cml

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038470/bt6831Isup4.cdx

checkCIF report


Comment top

Acid-related diseases are highly prevalent in the developed world, and the inhibition of the gastric proton pump enzyme (H+/K+-ATPase) represents a major approach in the development of drugs against these medical conditions (Palmer et al., 2010). Bisabolangelone, a sesquiterpene isolated from the roots of Angelica polymorpha Maxim with the traditional Tujia medicine name of Zijinsha (Fang et al., 2006), displayed attractive bioactivity such as anti-feeding and insecticidal effect (Muckensturm et al., 1981). Recently, we found bisabolangelone and its derivatives also exhibited remarkably preventive and therapeutic action on gastric ulcer, and its anti-ulcer mechanism might be related to inhibition of the H+/K+-ATPase and reduction of the secretion of H+ (Wang et al., 2009). With the aim of studying the relationship between its structure and H+/K+-ATPase inhibition activity, the catalytic hydrogenated reduction (Huang et al., 2012) and epoxidation of bisabolangelone were undertaken, and the structure determination of the target compound was conducted by X-ray single-crystal analysis for the first time.

Compared with the crystal structure of bisabolangelone (Wang et al., 2007), most bond lengths in the title compound are in the normal range of single or double bonds. The 6-membered ring C(1)—C(2)—C(3)—C(4)—C(5)—C(6) shows a distorted chair conformation [Φ = 319.3 (9)°, Θ = 146.4 (5)°, puckering amplitude (Q) = 0.485 (4)°]. The 5-membered ring O(2)—C(5)—C(6)—C(8)—C(10) adopts an envelope conformation with C(8) at the flap. Intermolecular O—H···O interactions link the molecules into infinite zigzag chains along the a axis, which contribute to the stability of the structure.

Related literature top

The title compound was synthesized as a potential gastric cytoprotective agent. For background to gastric diseases, see: Palmer et al. (2010). For pharmacological uses of bisabolangelone, a sesquiterpene isolated from the roots of Angelica polymorpha Maxim, see: Fang & Liao (2006); Muckensturm et al. (1981). Huang et al. (2012); Wang et al. (2009). For the crystal structure of bisabolangelone, see: Wang et al. (2007).

Experimental top

3-Hydroxy-3,6-dimethyl-2-(3-methylbut- 2-enylidene)-3,3a,7,7a-tetrahydrobenzofuran- 4(2H)-one (bisabolangelone, I, 1.00 g, 4.0 mmol) and Pd/C (0.10 g, 10% w/w) was dissolved in MeOH (30 ml) at 10\%C under dry nitrogen atmosphere, then hydrogen gas (99%) was bubbled into the vigorous stirred solution (50 ml/minute) for 2.0 h until the bisabolangelone was consumed. The hydrogen gas was diluted by large amounts of nitrogen and released into air through special pipeline, and the reaction mixture was filtered to recover the catalyst. Removing the solvents at reduced pressure to give white solids, which was purified by column chromatography on silica with ethyl acetate/petroleum ether (1:10, v/v) as eluent to give the pure intermediates 3-hydroxy-3,6-dimethyl-2-((E)-3-methylbut-1-enyl)hexahydrobenzofuran-4(2H)-one (II) as colorless needles (0.85 g). The m-CPBA (0.52 g, 1.5 mmol) and solid NaHCO3 (0.19 g, 2.5 mmol) were added to a solution of the intermediates II (0.25 g, 1.0 mmol) in dry CH2Cl2 (20 ml) at 0 °C. The solution was stirred for 10 h until complete consumption of the starting material. The reaction was quenched with saturated aqueous sodium thiosulfate solution and extracted with CH2Cl2 (3 × 15 ml). The combined organic extracts were washed with saturated aqueous NaHCO3 solution (25 ml) and dried over Na2SO4. The solventwas removed in vacuo and the residue purified by flash column chromatography on silica gel to give the pure (2S,3S,3aS,6S,7aR)-3-hydroxy-2-((2R,3S)-3-isopropyloxiran-2-yl)-3,6-dimethylhexahydrobenzofuran-4(2H)-one III (Eluant: ethyl acetate/petroleum ether = 1: 20, v/v). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a dilute solution of the title compound III in n-hexane:ethyl acetate, 10: 1 at room temperature.

Refinement top

Due to the absence of anomalous scatterers, the absolute configuration could not be determined and was arbitrarily set. Friedel pairs were merged. All H atoms were geometrically positioned and refined using a riding model with C—H = 0.93–0.97 Å and Uiso(methyl H) = 1.5 Ueq(C) and 1.2 Ueq(C, O) for other H atoms. The methyl and hydroxyl group were allowed to rotate but not to tip.

Structure description top

Acid-related diseases are highly prevalent in the developed world, and the inhibition of the gastric proton pump enzyme (H+/K+-ATPase) represents a major approach in the development of drugs against these medical conditions (Palmer et al., 2010). Bisabolangelone, a sesquiterpene isolated from the roots of Angelica polymorpha Maxim with the traditional Tujia medicine name of Zijinsha (Fang et al., 2006), displayed attractive bioactivity such as anti-feeding and insecticidal effect (Muckensturm et al., 1981). Recently, we found bisabolangelone and its derivatives also exhibited remarkably preventive and therapeutic action on gastric ulcer, and its anti-ulcer mechanism might be related to inhibition of the H+/K+-ATPase and reduction of the secretion of H+ (Wang et al., 2009). With the aim of studying the relationship between its structure and H+/K+-ATPase inhibition activity, the catalytic hydrogenated reduction (Huang et al., 2012) and epoxidation of bisabolangelone were undertaken, and the structure determination of the target compound was conducted by X-ray single-crystal analysis for the first time.

Compared with the crystal structure of bisabolangelone (Wang et al., 2007), most bond lengths in the title compound are in the normal range of single or double bonds. The 6-membered ring C(1)—C(2)—C(3)—C(4)—C(5)—C(6) shows a distorted chair conformation [Φ = 319.3 (9)°, Θ = 146.4 (5)°, puckering amplitude (Q) = 0.485 (4)°]. The 5-membered ring O(2)—C(5)—C(6)—C(8)—C(10) adopts an envelope conformation with C(8) at the flap. Intermolecular O—H···O interactions link the molecules into infinite zigzag chains along the a axis, which contribute to the stability of the structure.

The title compound was synthesized as a potential gastric cytoprotective agent. For background to gastric diseases, see: Palmer et al. (2010). For pharmacological uses of bisabolangelone, a sesquiterpene isolated from the roots of Angelica polymorpha Maxim, see: Fang & Liao (2006); Muckensturm et al. (1981). Huang et al. (2012); Wang et al. (2009). For the crystal structure of bisabolangelone, see: Wang et al. (2007).

Computing details top

Data collection: CrystalClear (Rigaku, 2011); cell refinement: CrystalClear (Rigaku, 2011); data reduction: CrystalClear (Rigaku, 2011); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atom ise presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A packing diagram for the title compound showing O—H···O intra-molecular hydrogen bonds (dashed lines).
(2S*,3S*,3aS*,6S*,7aR*)-3-Hydroxy- 2-[(2R*,3S*)-3-isopropyloxiran-2-yl]-3,6-dimethyl- 3,3a,5,6,7,7a-hexahydro-1-benzofuran-4(2H)-one top
Crystal data top
C15H24O4F(000) = 584
Mr = 268.34Dx = 1.158 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2058 reflections
a = 6.616 (7) Åθ = 2.7–27.5°
b = 9.261 (9) ŵ = 0.08 mm−1
c = 25.12 (3) ÅT = 296 K
V = 1539 (3) Å3Prism, colorless
Z = 40.35 × 0.28 × 0.26 mm
Data collection top
Rigaku model name? CCD area-detector
diffractometer		2058 independent reflections
Radiation source: fine-focus sealed tube1568 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.176
phi and ω scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2011)		h = −8→8
Tmin = 0.972, Tmax = 0.980k = −12→12
16467 measured reflectionsl = −32→32
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0887P)2 + 0.2181P]
where P = (Fo2 + 2Fc2)/3
2058 reflections(Δ/σ)max < 0.001
177 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C15H24O4V = 1539 (3) Å3
Mr = 268.34Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.616 (7) ŵ = 0.08 mm−1
b = 9.261 (9) ÅT = 296 K
c = 25.12 (3) Å0.35 × 0.28 × 0.26 mm
Data collection top
Rigaku model name? CCD area-detector
diffractometer		2058 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2011)		1568 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.980Rint = 0.176
16467 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.185H-atom parameters constrained
S = 1.03Δρmax = 0.20 e Å−3
2058 reflectionsΔρmin = −0.19 e Å−3
177 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
C10.3330 (6)0.7529 (5)0.08201 (17)0.0809 (11)
C20.2584 (5)0.8871 (5)0.05651 (16)0.0771 (11)
H2A0.20520.95010.08400.093*
H2B0.14740.86230.03300.093*
C30.4150 (6)0.9702 (5)0.02476 (14)0.0788 (11)
H30.46050.9093−0.00480.095*
C40.5947 (6)1.0012 (5)0.06053 (14)0.0793 (11)
H4A0.69261.05860.04110.095*
H4B0.55001.05720.09100.095*
C50.6938 (5)0.8657 (5)0.07967 (14)0.0748 (11)
H50.76930.82280.05010.090*
C60.5481 (5)0.7502 (4)0.10272 (15)0.0706 (9)
H60.60490.65510.09440.085*
C70.3260 (10)1.1082 (7)0.0018 (2)0.1196 (19)
H7A0.21371.0847−0.02080.179*
H7B0.42731.1577−0.01850.179*
H7C0.28081.16920.03030.179*
C80.5676 (5)0.7732 (3)0.16381 (14)0.0626 (8)
C90.5010 (8)0.6450 (4)0.1976 (2)0.0937 (14)
H9A0.52760.66500.23440.141*
H9B0.57450.56050.18690.141*
H9C0.35890.62880.19270.141*
C100.7945 (5)0.8060 (4)0.16665 (15)0.0658 (9)
H100.87020.71590.16210.079*
C110.8628 (4)0.8785 (4)0.21676 (13)0.0581 (8)
H110.79030.96700.22640.070*
C120.9471 (5)0.7963 (4)0.26096 (14)0.0634 (8)
H120.95200.69160.25540.076*
C130.9347 (5)0.8420 (4)0.31751 (14)0.0690 (9)
H130.92590.94770.31800.083*
C140.7449 (8)0.7838 (6)0.3432 (2)0.1076 (17)
H14A0.62930.81280.32270.161*
H14B0.73350.82120.37870.161*
H14C0.75140.68030.34450.161*
C151.1278 (9)0.7993 (8)0.3472 (2)0.1161 (19)
H15A1.13470.69610.35010.174*
H15B1.12620.84110.38220.174*
H15C1.24340.83410.32800.174*
O10.2253 (6)0.6483 (5)0.08748 (18)0.1301 (15)
O20.8347 (3)0.8990 (3)0.12242 (9)0.0749 (7)
O30.4646 (3)0.9014 (2)0.17901 (9)0.0613 (6)
H3A0.35510.88030.19220.092*
O41.0785 (3)0.8795 (4)0.22651 (11)0.0802 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.074 (2)0.087 (3)0.081 (2)−0.021 (2)−0.003 (2)−0.014 (2)
C20.0604 (18)0.100 (3)0.071 (2)−0.010 (2)0.0036 (16)−0.015 (2)
C30.080 (2)0.102 (3)0.0548 (17)−0.005 (2)0.0107 (18)−0.0113 (19)
C40.081 (2)0.093 (3)0.0630 (19)−0.022 (2)0.0109 (19)0.004 (2)
C50.0617 (17)0.106 (3)0.0564 (17)−0.009 (2)0.0154 (16)−0.022 (2)
C60.070 (2)0.0609 (18)0.081 (2)−0.0009 (17)0.0061 (18)−0.0212 (17)
C70.133 (4)0.135 (5)0.090 (3)−0.002 (4)−0.015 (3)0.025 (3)
C80.0639 (18)0.0495 (15)0.075 (2)−0.0059 (15)0.0072 (16)−0.0049 (15)
C90.095 (3)0.063 (2)0.123 (4)−0.020 (2)−0.008 (3)0.020 (2)
C100.0593 (17)0.0631 (19)0.075 (2)0.0080 (16)0.0098 (17)−0.0040 (18)
C110.0485 (15)0.0563 (17)0.0695 (18)0.0006 (14)0.0097 (14)0.0032 (15)
C120.0545 (16)0.0559 (16)0.080 (2)0.0060 (15)0.0053 (16)0.0029 (16)
C130.074 (2)0.0594 (17)0.073 (2)−0.0010 (17)0.0024 (18)0.0082 (16)
C140.129 (4)0.096 (3)0.098 (3)−0.018 (3)0.036 (3)0.012 (3)
C150.121 (4)0.128 (5)0.099 (3)0.023 (4)−0.028 (3)0.006 (3)
O10.124 (3)0.114 (3)0.153 (3)−0.058 (2)−0.045 (3)0.012 (3)
O20.0550 (12)0.104 (2)0.0660 (13)−0.0143 (14)0.0110 (11)−0.0024 (13)
O30.0545 (11)0.0597 (12)0.0696 (13)−0.0028 (10)0.0165 (10)−0.0034 (11)
O40.0488 (11)0.110 (2)0.0821 (16)−0.0093 (15)0.0106 (11)0.0071 (16)
Geometric parameters (Å, º) top
C1—O11.210 (6)C9—H9A0.9600
C1—C21.482 (7)C9—H9B0.9600
C1—C61.515 (6)C9—H9C0.9600
C2—C31.517 (6)C10—O21.431 (4)
C2—H2A0.9700C10—C111.497 (5)
C2—H2B0.9700C10—H100.9800
C3—C41.518 (5)C11—O41.448 (4)
C3—C71.520 (8)C11—C121.457 (5)
C3—H30.9800C11—H110.9800
C4—C51.495 (7)C12—O41.448 (4)
C4—H4A0.9700C12—C131.484 (5)
C4—H4B0.9700C12—H120.9800
C5—O21.455 (4)C13—C141.512 (6)
C5—C61.552 (6)C13—C151.531 (6)
C5—H50.9800C13—H130.9800
C6—C81.554 (5)C14—H14A0.9600
C6—H60.9800C14—H14B0.9600
C7—H7A0.9600C14—H14C0.9600
C7—H7B0.9600C15—H15A0.9600
C7—H7C0.9600C15—H15B0.9600
C8—O31.420 (4)C15—H15C0.9600
C8—C91.525 (5)O3—H3A0.8200
C8—C101.533 (5)
O1—C1—C2121.6 (4)C8—C9—H9A109.5
O1—C1—C6120.0 (5)C8—C9—H9B109.5
C2—C1—C6118.4 (4)H9A—C9—H9B109.5
C1—C2—C3115.2 (4)C8—C9—H9C109.5
C1—C2—H2A108.5H9A—C9—H9C109.5
C3—C2—H2A108.5H9B—C9—H9C109.5
C1—C2—H2B108.5O2—C10—C11109.1 (3)
C3—C2—H2B108.5O2—C10—C8105.4 (3)
H2A—C2—H2B107.5C11—C10—C8115.1 (3)
C4—C3—C7111.7 (4)O2—C10—H10109.1
C4—C3—C2108.6 (3)C11—C10—H10109.1
C7—C3—C2111.2 (4)C8—C10—H10109.1
C4—C3—H3108.4O4—C11—C1259.8 (2)
C7—C3—H3108.4O4—C11—C10116.3 (3)
C2—C3—H3108.4C12—C11—C10121.5 (3)
C5—C4—C3112.1 (4)O4—C11—H11115.8
C5—C4—H4A109.2C12—C11—H11115.8
C3—C4—H4A109.2C10—C11—H11115.8
C5—C4—H4B109.2O4—C12—C1159.8 (2)
C3—C4—H4B109.2O4—C12—C13116.9 (3)
H4A—C4—H4B107.9C11—C12—C13124.0 (3)
O2—C5—C4109.9 (3)O4—C12—H12114.9
O2—C5—C6105.6 (3)C11—C12—H12114.9
C4—C5—C6115.2 (3)C13—C12—H12114.9
O2—C5—H5108.7C12—C13—C14110.6 (4)
C4—C5—H5108.7C12—C13—C15110.3 (3)
C6—C5—H5108.7C14—C13—C15113.1 (4)
C1—C6—C5116.3 (4)C12—C13—H13107.5
C1—C6—C8114.5 (3)C14—C13—H13107.5
C5—C6—C8102.8 (3)C15—C13—H13107.5
C1—C6—H6107.6C13—C14—H14A109.5
C5—C6—H6107.6C13—C14—H14B109.5
C8—C6—H6107.6H14A—C14—H14B109.5
C3—C7—H7A109.5C13—C14—H14C109.5
C3—C7—H7B109.5H14A—C14—H14C109.5
H7A—C7—H7B109.5H14B—C14—H14C109.5
C3—C7—H7C109.5C13—C15—H15A109.5
H7A—C7—H7C109.5C13—C15—H15B109.5
H7B—C7—H7C109.5H15A—C15—H15B109.5
O3—C8—C9111.2 (3)C13—C15—H15C109.5
O3—C8—C10107.0 (3)H15A—C15—H15C109.5
C9—C8—C10114.3 (3)H15B—C15—H15C109.5
O3—C8—C6109.9 (3)C10—O2—C5109.0 (3)
C9—C8—C6114.7 (3)C8—O3—H3A109.5
C10—C8—C698.9 (3)C11—O4—C1260.4 (2)
O1—C1—C2—C3−146.8 (5)C9—C8—C10—O2164.2 (3)
C6—C1—C2—C334.8 (5)C6—C8—C10—O241.9 (3)
C1—C2—C3—C4−54.8 (5)O3—C8—C10—C1148.0 (4)
C1—C2—C3—C7−178.1 (4)C9—C8—C10—C11−75.6 (4)
C7—C3—C4—C5−175.3 (4)C6—C8—C10—C11162.1 (3)
C2—C3—C4—C561.8 (4)O2—C10—C11—O4−76.3 (4)
C3—C4—C5—O2−167.6 (3)C8—C10—C11—O4165.6 (3)
C3—C4—C5—C6−48.5 (4)O2—C10—C11—C12−145.5 (3)
O1—C1—C6—C5161.9 (4)C8—C10—C11—C1296.4 (4)
C2—C1—C6—C5−19.6 (5)C10—C11—C12—O4104.2 (3)
O1—C1—C6—C8−78.2 (6)O4—C11—C12—C13103.9 (4)
C2—C1—C6—C8100.2 (4)C10—C11—C12—C13−152.0 (3)
O2—C5—C6—C1148.0 (3)O4—C12—C13—C14160.0 (3)
C4—C5—C6—C126.6 (5)C11—C12—C13—C1489.8 (4)
O2—C5—C6—C822.0 (4)O4—C12—C13—C15−74.1 (4)
C4—C5—C6—C8−99.4 (3)C11—C12—C13—C15−144.3 (4)
C1—C6—C8—O3−53.2 (4)C11—C10—O2—C5−154.0 (3)
C5—C6—C8—O374.0 (3)C8—C10—O2—C5−29.9 (4)
C1—C6—C8—C973.1 (5)C4—C5—O2—C10129.2 (3)
C5—C6—C8—C9−159.8 (3)C6—C5—O2—C104.4 (4)
C1—C6—C8—C10−164.9 (3)C10—C11—O4—C12−112.7 (4)
C5—C6—C8—C10−37.8 (3)C13—C12—O4—C11−115.5 (3)
O3—C8—C10—O2−72.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O4i0.822.022.827 (4)166
Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC15H24O4
Mr268.34
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)6.616 (7), 9.261 (9), 25.12 (3)
V (Å3)1539 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.35 × 0.28 × 0.26
Data collection
DiffractometerRigaku model name? CCD area-detector
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2011)
Tmin, Tmax0.972, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections		16467, 2058, 1568
Rint0.176
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.185, 1.03
No. of reflections2058
No. of parameters177
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.20, −0.19

Computer programs: CrystalClear (Rigaku, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O4i0.822.022.827 (4)166.4
Symmetry code: (i) x−1, y, z.
 

Acknowledgements

We gratefully acknowledge financial support by the National Natural Science Foundation of China (Nos. 30970296 and 21102084), the Scientific and Technological Research Project of Hubei Provincial Department of Education (No. Q20111210), the Doctoral Startup Foundation of China Three Gorges University (No. KJ2009B046) and the Pre-research Foundation of the College of Chemistry and Life Sciences (No. HY0905).

References

First citationFang, Z. & Liao, Z. (2006). The Medicinal Plants from Enshi of Hubei. Wuhan, China: The Science and Technological Press of Hubei.  Google Scholar
 First citationHuang, N. Y., Chen, L., Liao, Z. J., Fang, H. B., Wang, J. Z. & Zou, K. (2012). Chin. J. Chem. 30, 71–76.  Web of Science CSD CrossRef CAS Google Scholar
 First citationMuckensturm, B., Duplay, D., Robert, P. C., Simonis, M. T. & Kienlen, J. C. (1981). Biochem. Syst. Ecol. 2, 289–292.  CrossRef Web of Science Google Scholar
 First citationPalmer, A. M., Chiesa, V., Schmid, A., Muench, G., Grobbel, B., Zimmermann, P. J., Brehm, C., Buhr, W., Simon, W.-A., Kromer, W., Postius, S., Volz, J. & Hess, D. (2010). J. Med. Chem. 53, 3645–3674.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationRigaku (2011). CrystalClear. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, J. Z., Zhu, L. B., Zou, K., Cheng, F., Dan, F. J., Guo, Z. Y., Cai, Z. J. & Yang, J. (2009). J. Ethnopharma. 123, 343–346.  Web of Science CrossRef Google Scholar
 First citationWang, J.-Z., Zou, K., Cheng, F. & Dan, F.-J. (2007). Acta Cryst. E63, o2706.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2949
https://doi.org/10.1107/S1600536812038470
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS