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

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ISSN: 2056-9890

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

aHainan Provincial Key Laboratory of Tropical Pharmaceutical Herb Chemistry, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China
*Correspondence e-mail: chgying123@163.com, hchr116@hainnu.edu.cn

(Received 26 September 2009; accepted 13 October 2009; online 23 October 2009)

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[Tempeam, A., Thasana, N., Pavaro, C., Chuakul, W., Siripong, P. & Ruchirawat, S. (2005). Chem. Pharm. Bull. 53, 1321-1323.]); Chen et al. (2009[Chen, H. D., He, X. F., Ai, J., Geng, M. Y. & Yue, J. M. (2009). Org. Lett. 11, 4080-4083.]). For medicinal applications of this family of compounds, see: Chuakul et al. (1997[Chuakul, W., Saralump, P. & Prathanturarug, S. (1997). Medicinal Plants in Thailand, Vol. II, pp. 192-193. Bangkok: Amarin Printing and Publishing Public Co Ltd.]); Tempeam et al. (2002[Tempeam, A., Thasana, N., Thavornkitcharat, A., Pavaro, C. & Ruchirawat, S. (2002). J. Pharm. Sci. 29, 25-31.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14O4

  • Mr = 210.22

  • Monoclinic, P 21 /c

  • 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[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.066, Tmax = 0.185

  • 7549 measured reflections

  • 2673 independent reflections

  • 1749 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.094

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2 0.82 1.86 2.577 (4) 146

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

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.

Related literature top

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

Experimental top

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 top

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).

Structure description top

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.

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

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: SHELXP-97 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of (I) with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the molecular packing for (I).
1-(2-Hydroxy-4,5-dimethoxyphenyl)propan-1-one top
Crystal data top
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 top
Bruker SMART CCD
diffractometer
2673 independent reflections
Radiation source: fine-focus sealed tube1749 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
ω scansθmax = 28.4°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 99
Tmin = 0.066, Tmax = 0.185k = 1212
7549 measured reflectionsl = 2213
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)] = 0.094Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.295H-atom parameters constrained
S = 1.12 w = 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
Crystal data top
C11H14O4V = 1079.1 (2) Å3
Mr = 210.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.1933 (7) ŵ = 0.10 mm1
b = 9.4874 (12) ÅT = 293 K
c = 17.198 (2) Å0.31 × 0.16 × 0.14 mm
β = 113.164 (5)°
Data collection top
Bruker SMART CCD
diffractometer
2673 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
1749 reflections with I > 2σ(I)
Tmin = 0.066, Tmax = 0.185Rint = 0.044
7549 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0940 restraints
wR(F2) = 0.295H-atom parameters constrained
S = 1.12Δρmax = 0.41 e Å3
2673 reflectionsΔρmin = 0.28 e Å3
136 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
O10.3767 (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)
H30.16240.07760.43640.080*
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)
H8A0.05290.04760.31110.080*
H8B0.15450.01200.30610.080*
C90.0065 (8)0.1589 (5)0.2186 (3)0.0801 (14)
H9A0.06990.09020.17520.080*
H9B0.10770.19900.21100.080*
H9C0.10170.23190.21520.080*
C100.1800 (6)0.3028 (4)0.5156 (2)0.0600 (10)
H10A0.17140.39450.53760.080*
H10B0.26210.30790.48310.080*
H10C0.04690.27090.48010.080*
C110.5335 (7)0.0537 (5)0.7830 (2)0.0699 (12)
H11A0.56840.00030.83400.080*
H11B0.43640.12460.78090.080*
H11C0.65270.09800.78210.080*
Atomic displacement parameters (Å2) top
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, º) top
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, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.862.577 (4)146

Experimental details

Crystal data
Chemical formulaC11H14O4
Mr210.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.1933 (7), 9.4874 (12), 17.198 (2)
β (°) 113.164 (5)
V3)1079.1 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.31 × 0.16 × 0.14
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.066, 0.185
No. of measured, independent and
observed [I > 2σ(I)] reflections
7549, 2673, 1749
Rint0.044
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.094, 0.295, 1.12
No. of reflections2673
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.41, 0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXP-97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.862.577 (4)146
 

Acknowledgements

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.

References

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

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