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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2815.
Published online 2009 October 23. doi:  10.1107/S1600536809041798
PMCID: PMC2971157

1-(2-Hydr­oxy-4,5-dimeth­oxyphen­yl)propan-1-one

Abstract

In the title compound, C11H14O4, isolated from the stems of Trigonostemon xyphophylloides, an intra­molecular O—H(...)O hydrogen bond helps to establish an essentially planar conformation for the mol­ecule (r.m.s. deviation = 0.044 Å).

Related literature

For botanical and biochemical background, see: Tempeam et al. (2005 [triangle]); Chen et al. (2009 [triangle]). For medicinal applications of this family of compounds, see: Chuakul et al. (1997 [triangle]); Tempeam et al. (2002 [triangle]).

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Object name is e-65-o2815-scheme1.jpg

Experimental

Crystal data

  • C11H14O4
  • M r = 210.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2815-efi1.jpg
  • a = 7.1933 (7) Å
  • b = 9.4874 (12) Å
  • c = 17.198 (2) Å
  • β = 113.164 (5)°
  • V = 1079.1 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.31 × 0.16 × 0.14 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.066, T max = 0.185
  • 7549 measured reflections
  • 2673 independent reflections
  • 1749 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.094
  • wR(F 2) = 0.295
  • S = 1.12
  • 2673 reflections
  • 136 parameters
  • H-atom parameters constrained
  • Δρmax = 0.41 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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 global, I. DOI: 10.1107/S1600536809041798/hb5121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041798/hb5121Isup2.hkl

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (20862005), the Program for New Century Excellent Talents in Universities (NCET-08–0656), the Natural Science Foundation of Hainan Province (No. 070207) and the University Graduate Student Innovation Science Research Project of Hainan Province (No. Hxwsy2008–17). We thank Bingjing Xin for collecting the crystal data.

supplementary crystallographic information

Comment

Secondary metabolites in the plants of Trigonostemon xyphophylloides are mainly daphnane diterpenoids, phenanthrenones, alkaloids and coumarins (Tempeam et al., 2005; Chen et al., 2009). The plants in this family were used in folk medicine such as an emetic for food poisoning, a laxative and an anti-asthmatic, has also been used in the treatment of bloody and mucous sputum or stool. It was applied to reduce abscesses and to alleviate sprains, swelling and bruizes, is particularly effective in treating snake bites especially against snake neurotoxins. (Chuakul et al., 1997; Tempeam et al., 2002). The title compound was isolated from the 75% EtOH extract of the stems of Trigonostemon xyphophylloides which were collected from Jianfengling County, Hainan Province, P. R. China. We have undertaken the X-ray crystal structure analysis of the title compound in order to establish its molecular structure and relative stereochemistry.

The hydrogen bonds and angles are listed in Table 1.

Experimental

Air-dried stems of Trigonostemon xyphophylloides (5.9 kg) were ground and percolated (3 × 2.5 h) with 75% EtOH at 333 K, which was suspended in 1.5 l water and then partitioned with petroleum ether, chloroform, ethyl acetate and n-BuOH, successively, yielding a petroleum ether extract, a chloroform extract, an ethyl acetate extract and a n-BuOH extract, respectively. The petroleum ether extract was subjected to a silica gel CC column using petroleum ether as first eluent and then increasing the polarity with EtOAc, to afford 20 fractions (A—T). Fraction D was further separated by column chromatography with a gradient of petroleum ether-EtOAc to give the title compound. The crude product was dissolved in small amount of ethyl acetate to obtain colourless blocks of (I) by slow evaporation of ethyl acetate solution at 298 K.

Refinement

H atoms bonded to C atoms were palced in geometrically calculated position and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C). H atoms attached to O atoms were found in a difference Fourier synthesis and were refined using a riding model, with the O—H distances fixed as initially found and with Uiso(H) values set at 1.5 Ueq(O).

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
A view of the molecular packing for (I).

Crystal data

C11H14O4F(000) = 448
Mr = 210.22Dx = 1.294 Mg m3
Monoclinic, P21/cMelting point: not measured K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.1933 (7) ÅCell parameters from 2673 reflections
b = 9.4874 (12) Åθ = 2.5–28.4°
c = 17.198 (2) ŵ = 0.10 mm1
β = 113.164 (5)°T = 293 K
V = 1079.1 (2) Å3Block, colourless
Z = 40.31 × 0.16 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer2673 independent reflections
Radiation source: fine-focus sealed tube1749 reflections with I > 2σ(I)
graphiteRint = 0.044
ω scansθmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)h = −9→9
Tmin = 0.066, Tmax = 0.185k = −12→12
7549 measured reflectionsl = −22→13

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)] = 0.094Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.295H-atom parameters constrained
S = 1.12w = 1/[σ2(Fo2) + (0.1225P)2 + 1.1131P] where P = (Fo2 + 2Fc2)/3
2673 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = −0.28 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
O10.3767 (5)0.3553 (3)0.52714 (19)0.0723 (9)
H10.33230.37570.47680.080*
O20.1907 (5)0.3117 (3)0.36706 (18)0.0763 (9)
O30.2687 (4)−0.2066 (3)0.58386 (15)0.0600 (8)
O40.4475 (4)−0.0386 (3)0.71051 (14)0.0581 (7)
C10.3465 (5)0.2161 (4)0.5358 (2)0.0497 (8)
C20.2485 (5)0.1275 (3)0.4653 (2)0.0435 (7)
C30.2245 (5)−0.0169 (4)0.48170 (19)0.0437 (7)
H30.1624−0.07760.43640.080*
C40.2907 (5)−0.0694 (3)0.5629 (2)0.0432 (7)
C50.3876 (5)0.0225 (4)0.63263 (19)0.0441 (7)
C60.4134 (5)0.1631 (4)0.6178 (2)0.0499 (8)
H60.47640.22320.66330.080*
C70.1702 (5)0.1852 (4)0.3788 (2)0.0509 (8)
C80.0636 (6)0.0885 (4)0.3045 (2)0.0569 (9)
H8A−0.05290.04760.31110.080*
H8B0.15450.01200.30610.080*
C9−0.0065 (8)0.1589 (5)0.2186 (3)0.0801 (14)
H9A−0.06990.09020.17520.080*
H9B0.10770.19900.21100.080*
H9C−0.10170.23190.21520.080*
C100.1800 (6)−0.3028 (4)0.5156 (2)0.0600 (10)
H10A0.1714−0.39450.53760.080*
H10B0.2621−0.30790.48310.080*
H10C0.0469−0.27090.48010.080*
C110.5335 (7)0.0537 (5)0.7830 (2)0.0699 (12)
H11A0.5684−0.00030.83400.080*
H11B0.43640.12460.78090.080*
H11C0.65270.09800.78210.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.107 (2)0.0456 (15)0.0605 (17)−0.0084 (14)0.0294 (16)−0.0016 (13)
O20.115 (3)0.0534 (17)0.0561 (16)−0.0070 (16)0.0287 (17)0.0092 (13)
O30.0858 (18)0.0402 (13)0.0372 (12)−0.0007 (12)0.0062 (12)0.0020 (10)
O40.0790 (17)0.0490 (14)0.0347 (12)−0.0005 (12)0.0098 (11)−0.0045 (10)
C10.0556 (19)0.0434 (18)0.0509 (18)0.0009 (15)0.0219 (15)−0.0022 (14)
C20.0482 (17)0.0395 (16)0.0422 (16)0.0051 (13)0.0170 (13)−0.0005 (13)
C30.0472 (17)0.0426 (17)0.0377 (15)0.0044 (13)0.0129 (13)−0.0046 (13)
C40.0444 (16)0.0399 (16)0.0413 (16)0.0072 (13)0.0125 (13)−0.0007 (13)
C50.0459 (16)0.0452 (17)0.0371 (15)0.0061 (14)0.0120 (12)−0.0036 (13)
C60.0551 (19)0.0473 (19)0.0437 (17)0.0005 (15)0.0155 (15)−0.0091 (14)
C70.058 (2)0.048 (2)0.0461 (18)0.0053 (15)0.0200 (15)0.0048 (15)
C80.069 (2)0.057 (2)0.0405 (17)0.0013 (17)0.0162 (16)0.0066 (15)
C90.107 (4)0.073 (3)0.045 (2)0.001 (3)0.013 (2)0.012 (2)
C100.078 (3)0.0443 (19)0.0439 (18)0.0030 (17)0.0091 (17)−0.0015 (15)
C110.098 (3)0.065 (3)0.0358 (17)−0.002 (2)0.0149 (19)−0.0100 (17)

Geometric parameters (Å, °)

O1—C11.355 (4)C6—H60.9300
O1—H10.8200C7—C81.513 (5)
O2—C71.235 (4)C8—C91.516 (5)
O3—C41.376 (4)C8—H8A0.9700
O3—C101.424 (4)C8—H8B0.9700
O4—C51.364 (4)C9—H9A0.9600
O4—C111.448 (4)C9—H9B0.9600
C1—C61.393 (5)C9—H9C0.9600
C1—C21.415 (5)C10—H10A0.9600
C2—C31.423 (5)C10—H10B0.9600
C2—C71.473 (5)C10—H10C0.9600
C3—C41.379 (4)C11—H11A0.9600
C3—H30.9300C11—H11B0.9600
C4—C51.423 (4)C11—H11C0.9600
C5—C61.385 (5)
C1—O1—H1109.5C7—C8—C9114.8 (3)
C4—O3—C10116.8 (3)C7—C8—H8A108.6
C5—O4—C11116.8 (3)C9—C8—H8A108.6
O1—C1—C6117.2 (3)C7—C8—H8B108.6
O1—C1—C2122.2 (3)C9—C8—H8B108.6
C6—C1—C2120.7 (3)H8A—C8—H8B107.5
C1—C2—C3117.4 (3)C8—C9—H9A109.5
C1—C2—C7120.5 (3)C8—C9—H9B109.5
C3—C2—C7122.0 (3)H9A—C9—H9B109.5
C4—C3—C2121.9 (3)C8—C9—H9C109.5
C4—C3—H3119.1H9A—C9—H9C109.5
C2—C3—H3119.1H9B—C9—H9C109.5
O3—C4—C3125.3 (3)O3—C10—H10A109.5
O3—C4—C5115.3 (3)O3—C10—H10B109.5
C3—C4—C5119.4 (3)H10A—C10—H10B109.5
O4—C5—C6125.2 (3)O3—C10—H10C109.5
O4—C5—C4115.3 (3)H10A—C10—H10C109.5
C6—C5—C4119.4 (3)H10B—C10—H10C109.5
C5—C6—C1121.1 (3)O4—C11—H11A109.5
C5—C6—H6119.4O4—C11—H11B109.5
C1—C6—H6119.4H11A—C11—H11B109.5
O2—C7—C2120.2 (3)O4—C11—H11C109.5
O2—C7—C8120.3 (3)H11A—C11—H11C109.5
C2—C7—C8119.5 (3)H11B—C11—H11C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.862.577 (4)146

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5121).

References

  • Bruker (1997). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, H. D., He, X. F., Ai, J., Geng, M. Y. & Yue, J. M. (2009). Org. Lett.11, 4080–4083. [PubMed]
  • Chuakul, W., Saralump, P. & Prathanturarug, S. (1997). Medicinal Plants in Thailand, Vol. II, pp. 192–193. Bangkok: Amarin Printing and Publishing Public Co Ltd.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tempeam, A., Thasana, N., Pavaro, C., Chuakul, W., Siripong, P. & Ruchirawat, S. (2005). Chem. Pharm. Bull.53, 1321–1323. [PubMed]
  • Tempeam, A., Thasana, N., Thavornkitcharat, A., Pavaro, C. & Ruchirawat, S. (2002). J. Pharm. Sci.29, 25–31.

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