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

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ISSN: 2056-9890

3-Hy­dr­oxy-1,2-dimeth­oxyxanthone

aDepartment of Mathematics and Physics, Shanghai University of Electric Power, Shanghai 200090, People's Republic of China, and bDepartment of Pharmacy, Changzheng Hospital, Second Military Medical University, Shanghai 200003, People's Republic of China
*Correspondence e-mail: wuzhijun999@sina.com

(Received 9 May 2011; accepted 4 June 2011; online 18 June 2011)

The title compound (systematic name: 3-hy­droxy-1,2-dimeth­oxy-9H-xanthen-9-one), C15H12O5, was isolated from Polygala arillata. The tricyclic unit is essentially planar (r.m.s. deviation = 0.039 Å). In the crystal, the mol­ecules form stacks along the a axis. Inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains parallel to [010].

Related literature

For general background to the title compound and the plant Polygala arillata, see: Corrêa et al. (1970[Corrêa, D. B., Fonseca e Silva, L. G., Gottlieb, O. R. & Gonçalves, S. J. (1970). Phytochemistry, 9, 447-451.]); De Oliveira et al. (1968[De Oliveira, G., Mesquita, A. A. L., Gottlieb, O. R. & Magalhaes, M. T. (1968). An. Acad. Bras. Cienc., 40, 29-31.]); Dominguez et al. (1990[Dominguez, S. X. A., Sosa, U. M. G., Ortiz, C. & Jakupovic, J. (1990). Planta Med., 56, 126-127.]); Gottlieb et al. (1970[Gottlieb, O. R., Mesquita, A. A. L., De Oliveira, G. G. & Teixeira De Melo, M. (1970). Phytochemistry, 9, 2537-2544.]); Jiangshu New Medicinal College (1977[Jiangshu New Medicinal College (1977). Dictionary of Chinese Drugs, p. 2071. Shanghai Scientific Technologic Publisher.]); Li et al. (1999[Li, W. W., Xiao, P. G., Chen, S. L., Liang, X. Y. & Yang, X. X. (1999). Zhongguo Zhongyao Zazhi, 24, 477-479.]); Lin et al. (2005[Lin, L., Huang, F., Chen, S. B., Yang, D. J., Chen, S. L., Yang, J. S. & Xiao, P. G. (2005). Zhongguo Zhongyao Zazhi, 30, 827-830.]); Miao et al. (1996[Miao, S. L., Liao, S. X., Wu, J. H., Liang, H. Q., Chen, H. S. & Zhang, C. K. (1996). Acta Pharmaceutica Sinica, 31, 118-121.], 1997[Miao, S. L., Liao, S. X., Wu, J. H., Ling, N., Chen, H., Liang, H. Q. & Liu, M. Z. (1997). Acta Pharm. Sin. 32, 360-362.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12O5

  • Mr = 272.25

  • Triclinic, [P \overline 1]

  • a = 7.338 (2) Å

  • b = 7.824 (3) Å

  • c = 11.964 (4) Å

  • α = 94.634 (4)°

  • β = 93.561 (4)°

  • γ = 115.027 (4)°

  • V = 616.8 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 293 K

  • 0.15 × 0.12 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.984, Tmax = 0.989

  • 2562 measured reflections

  • 2126 independent reflections

  • 1697 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.190

  • S = 1.07

  • 2126 reflections

  • 184 parameters

  • H-atom parameters constrained

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5⋯O2i 0.82 1.90 2.713 (3) 169
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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


Comment top

Polygala arillata Buch-Ham is mainly distributed in south-west of China. The roots of Polygala arillata has been used in Chinese folk medicine to treat expectorant, hepatitis, pneumonia and rheumatism (Jiangshu New Medicinal College, 1977). Some chemical constituents of this plant have been reported previously (Miao et al., 1996, 1997; Li et al., 1999). Our chemical investigation of this plant for bioactive components resulted in the isolation of the title compound, which was previously obtained from Kielmeyera rupestris (Corrêa et al., 1970), Kielmeyera speciosa (De Oliveira et al., 1968, Gottlieb et al., 1970), Polygala nitida (Dominguez et al., 1990) and Polygala fallax (Lin et al., 2005). Herein we report the crystal structure determination of the title compound.

Related literature top

For general background to the title compound and the plant Polygala arillata, see: Corrêa et al. (1970); De Oliveira et al. (1968); Dominguez et al. (1990); Gottlieb et al. (1970); Jiangshu New Medicinal College (1977); Li et al. (1999); Lin et al. (2005); Miao et al. (1996, 1997).

Experimental top

Three 5 kg portions of dry powdered stem bark of Polygala arillata were refluxed for 1 h with 95% ethanol (50L). After removal of ethanol under reduced pressure, the extract was suspended in water and then partitioned with chloroform, ethyl acetate and n-butanol. The chloroform soluble fraction (50 g) was subjected to silica gel column chromatography using gradient elution (petroleum ether/acetone, 10:1 to 2:1, v/v). 3-hydroxy-1,2-dimethoxyxanthone was obtained from the fraction eluted by 3:1 petroleum ether/acetone ratio. Single crystals suitable for X-ray diffraction analysis were grown by slow evaporation of acetone solution at room temperature.

Refinement top

The hydroxyl H atoms attached to O5 was located by a difference Fourier map and refined isotropically with a restrained O–H distance 0.82 Å. The remaining H atoms were placed in calculated positions with C—H distances in the range 0.93–0.98 Å. The Uĩso~ values were set equal to 1.2Ueq (C,O) for methyl and hydroxyl H atoms and 1.5Ueq(C) for the remaining H atoms.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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, showing the atom-labelling scheme and displacement ellipsoids drawn at the 30% probability level.
3-Hydroxy-1,2-dimethoxy-9H-xanthen-9-one top
Crystal data top
C15H12O5Z = 2
Mr = 272.25F(000) = 284
Triclinic, P1Dx = 1.466 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.338 (2) ÅCell parameters from 804 reflections
b = 7.824 (3) Åθ = 2.9–27.3°
c = 11.964 (4) ŵ = 0.11 mm1
α = 94.634 (4)°T = 293 K
β = 93.561 (4)°Block, colourless
γ = 115.027 (4)°0.15 × 0.12 × 0.10 mm
V = 616.8 (3) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2126 independent reflections
Radiation source: fine-focus sealed tube1697 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
ϕ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 68
Tmin = 0.984, Tmax = 0.989k = 95
2562 measured reflectionsl = 1314
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1114P)2 + 0.1836P]
where P = (Fo2 + 2Fc2)/3
2126 reflections(Δ/σ)max < 0.001
184 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C15H12O5γ = 115.027 (4)°
Mr = 272.25V = 616.8 (3) Å3
Triclinic, P1Z = 2
a = 7.338 (2) ÅMo Kα radiation
b = 7.824 (3) ŵ = 0.11 mm1
c = 11.964 (4) ÅT = 293 K
α = 94.634 (4)°0.15 × 0.12 × 0.10 mm
β = 93.561 (4)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2126 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1697 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.989Rint = 0.037
2562 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.190H-atom parameters constrained
S = 1.07Δρmax = 0.23 e Å3
2126 reflectionsΔρmin = 0.32 e Å3
184 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 > 2σ(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
O10.2867 (3)0.6977 (2)0.52398 (13)0.0473 (5)
O20.2172 (3)0.1946 (2)0.35370 (16)0.0603 (6)
O30.2629 (2)0.3673 (2)0.15973 (14)0.0498 (5)
O40.2920 (3)0.6826 (2)0.06394 (14)0.0544 (5)
O50.3176 (3)0.9927 (2)0.19396 (15)0.0592 (6)
H50.29211.06540.23650.089*
C10.2721 (3)0.5208 (3)0.22752 (19)0.0396 (5)
C20.2933 (3)0.6818 (3)0.17897 (19)0.0434 (6)
C30.3077 (3)0.8442 (3)0.2474 (2)0.0446 (6)
C40.3094 (3)0.8437 (3)0.3620 (2)0.0444 (6)
H40.32530.95200.40770.053*
C50.2517 (4)0.5696 (4)0.6956 (2)0.0534 (6)
H5A0.27080.68660.73170.064*
C60.2189 (4)0.4191 (4)0.7557 (2)0.0599 (7)
H60.21480.43430.83330.072*
C70.1919 (4)0.2451 (4)0.7025 (2)0.0599 (7)
H70.16890.14420.74440.072*
C80.1988 (4)0.2210 (4)0.5886 (2)0.0522 (6)
H80.18270.10410.55370.063*
C90.2376 (3)0.3482 (3)0.4018 (2)0.0417 (6)
C100.2654 (3)0.5149 (3)0.34488 (19)0.0376 (5)
C110.2873 (3)0.6818 (3)0.4091 (2)0.0397 (5)
C120.2559 (3)0.5436 (3)0.5796 (2)0.0437 (6)
C130.2302 (3)0.3713 (3)0.5240 (2)0.0422 (6)
C140.0691 (5)0.2530 (4)0.0989 (3)0.0700 (8)
H14A0.02790.19770.15110.105*
H14B0.07700.15390.04960.105*
H14C0.02780.33060.05510.105*
C150.4879 (5)0.7613 (5)0.0279 (3)0.0741 (9)
H15A0.56200.88910.06370.111*
H15B0.47720.76150.05240.111*
H15C0.55750.68650.04810.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0617 (10)0.0392 (9)0.0448 (9)0.0267 (8)0.0019 (8)0.0002 (7)
O20.0869 (14)0.0343 (9)0.0675 (12)0.0328 (9)0.0145 (10)0.0052 (8)
O30.0571 (10)0.0413 (9)0.0539 (10)0.0275 (8)0.0010 (8)0.0093 (7)
O40.0648 (11)0.0587 (11)0.0442 (10)0.0317 (9)0.0002 (8)0.0053 (8)
O50.0896 (14)0.0429 (10)0.0591 (11)0.0397 (10)0.0147 (10)0.0137 (8)
C10.0373 (11)0.0346 (11)0.0480 (13)0.0186 (9)0.0005 (9)0.0032 (9)
C20.0447 (12)0.0424 (13)0.0455 (13)0.0220 (10)0.0022 (10)0.0017 (10)
C30.0487 (13)0.0353 (12)0.0548 (14)0.0226 (10)0.0049 (10)0.0077 (10)
C40.0525 (13)0.0335 (12)0.0525 (14)0.0248 (10)0.0037 (11)0.0005 (10)
C50.0511 (14)0.0574 (15)0.0497 (14)0.0230 (12)0.0003 (11)0.0013 (11)
C60.0504 (14)0.0740 (19)0.0502 (15)0.0208 (13)0.0029 (11)0.0154 (13)
C70.0504 (14)0.0602 (17)0.0641 (17)0.0164 (12)0.0021 (12)0.0250 (13)
C80.0459 (13)0.0433 (13)0.0665 (16)0.0172 (11)0.0046 (11)0.0136 (11)
C90.0378 (11)0.0332 (11)0.0577 (14)0.0190 (9)0.0048 (10)0.0034 (10)
C100.0335 (11)0.0307 (11)0.0503 (13)0.0161 (8)0.0026 (9)0.0027 (9)
C110.0399 (11)0.0364 (12)0.0457 (12)0.0202 (9)0.0018 (9)0.0008 (9)
C120.0380 (11)0.0439 (13)0.0506 (13)0.0188 (10)0.0032 (9)0.0077 (10)
C130.0327 (11)0.0404 (13)0.0543 (14)0.0163 (9)0.0034 (10)0.0086 (10)
C140.0711 (18)0.0511 (16)0.078 (2)0.0234 (13)0.0121 (15)0.0171 (14)
C150.085 (2)0.083 (2)0.0597 (17)0.0379 (17)0.0243 (16)0.0156 (15)
Geometric parameters (Å, º) top
O1—C121.366 (3)C5—H5A0.9300
O1—C111.370 (3)C6—C71.383 (4)
O2—C91.234 (3)C6—H60.9300
O3—C11.368 (3)C7—C81.367 (4)
O3—C141.430 (3)C7—H70.9300
O4—C21.376 (3)C8—C131.405 (3)
O4—C151.415 (3)C8—H80.9300
O5—C31.349 (3)C9—C101.463 (3)
O5—H50.8200C9—C131.466 (3)
C1—C21.383 (3)C10—C111.402 (3)
C1—C101.412 (3)C12—C131.386 (3)
C2—C31.415 (3)C14—H14A0.9600
C3—C41.370 (3)C14—H14B0.9600
C4—C111.379 (3)C14—H14C0.9600
C4—H40.9300C15—H15A0.9600
C5—C61.370 (4)C15—H15B0.9600
C5—C121.391 (4)C15—H15C0.9600
C12—O1—C11119.52 (18)O2—C9—C10124.6 (2)
C1—O3—C14114.41 (19)O2—C9—C13120.0 (2)
C2—O4—C15113.4 (2)C10—C9—C13115.45 (19)
C3—O5—H5109.5C11—C10—C1116.5 (2)
O3—C1—C2118.6 (2)C11—C10—C9119.1 (2)
O3—C1—C10120.1 (2)C1—C10—C9124.3 (2)
C2—C1—C10121.2 (2)O1—C11—C4114.15 (19)
O4—C2—C1120.4 (2)O1—C11—C10123.0 (2)
O4—C2—C3119.7 (2)C4—C11—C10122.9 (2)
C1—C2—C3119.8 (2)O1—C12—C13122.1 (2)
O5—C3—C4123.5 (2)O1—C12—C5116.1 (2)
O5—C3—C2116.7 (2)C13—C12—C5121.8 (2)
C4—C3—C2119.7 (2)C12—C13—C8117.8 (2)
C3—C4—C11119.7 (2)C12—C13—C9120.7 (2)
C3—C4—H4120.2C8—C13—C9121.4 (2)
C11—C4—H4120.2O3—C14—H14A109.5
C6—C5—C12118.6 (3)O3—C14—H14B109.5
C6—C5—H5A120.7H14A—C14—H14B109.5
C12—C5—H5A120.7O3—C14—H14C109.5
C5—C6—C7120.9 (3)H14A—C14—H14C109.5
C5—C6—H6119.6H14B—C14—H14C109.5
C7—C6—H6119.6O4—C15—H15A109.5
C8—C7—C6120.3 (2)O4—C15—H15B109.5
C8—C7—H7119.9H15A—C15—H15B109.5
C6—C7—H7119.9O4—C15—H15C109.5
C7—C8—C13120.5 (3)H15A—C15—H15C109.5
C7—C8—H8119.7H15B—C15—H15C109.5
C13—C8—H8119.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O2i0.821.902.713 (3)169
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H12O5
Mr272.25
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.338 (2), 7.824 (3), 11.964 (4)
α, β, γ (°)94.634 (4), 93.561 (4), 115.027 (4)
V3)616.8 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.15 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.984, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
2562, 2126, 1697
Rint0.037
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.190, 1.07
No. of reflections2126
No. of parameters184
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.32

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O2i0.821.902.713 (3)169
Symmetry code: (i) x, y+1, z.
 

Acknowledgements

The authors thank Dr Zhen-Xia Chen (Department of Chemistry, Fudan University, Shanghai) for the structure analysis.

References

First citationBruker (1997). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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First citationDe Oliveira, G., Mesquita, A. A. L., Gottlieb, O. R. & Magalhaes, M. T. (1968). An. Acad. Bras. Cienc., 40, 29–31.  CAS Google Scholar
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First citationMiao, S. L., Liao, S. X., Wu, J. H., Liang, H. Q., Chen, H. S. & Zhang, C. K. (1996). Acta Pharmaceutica Sinica, 31, 118–121.  Google Scholar
First citationMiao, S. L., Liao, S. X., Wu, J. H., Ling, N., Chen, H., Liang, H. Q. & Liu, M. Z. (1997). Acta Pharm. Sin. 32, 360–362.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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