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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2944.
Published online 2010 October 30. doi:  10.1107/S1600536810042674
PMCID: PMC3009218

(E)-1-(2-Hy­droxy-4,6-dimeth­oxy­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one from Kaempferia rotunda Val.

Abstract

The planar –CH=CHC(=O)– fragment (r.m.s. deviation = 0.074 Å) in the title compound, C18H18O5, connects the planar hy­droxy­dimeth­oxy­phenyl (r.m.s. deviation = 0.039 Å) and meth­oxy­lphenyl (r.m.s. deviation = 0.021 Å) parts. The central fragment forms a dihedral angle of 13.7 (1)° with the hy­droxy­dimeth­oxy­phenyl part and 32.0 (1)° with the meth­oxy­phenyl part. The hy­droxy group forms an intra­molecular hydrogen bond to the carbonyl O atom.

Related literature

For the isolation of the compound from Kaempferia rotunda, see: Sirat et al. (2001 [triangle]); Stevenson et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2944-scheme1.jpg

Experimental

Crystal data

  • C18H18O5
  • M r = 314.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2944-efi1.jpg
  • a = 12.8502 (8) Å
  • b = 8.3226 (5) Å
  • c = 14.1865 (9) Å
  • β = 97.765 (1)°
  • V = 1503.29 (16) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.45 × 0.40 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 13992 measured reflections
  • 3464 independent reflections
  • 2989 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.101
  • S = 1.01
  • 3464 reflections
  • 215 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042674/bt5385sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042674/bt5385Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Kaempferia rotunda is one of the four Malaysian Kaempferia of the Zingiberaceae family; among the constitutents isolated is 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one (Scheme I) (Sirat et al., 2001; Stevenson et al., 2007). The planar –CH═CHC(═O)– fragment (r.m.s. deviation 0.074 Å) connects the planar hydroxyldimethoxyphenyl (r.m.s. deviation 0.039 Å) and methoxylphenyl (r.m.s. deviation 0.021 Å) parts. The fragment is aligned at 13.7 (1) ° with the hydroxydimethoxyphenyl part and at 32.0 (1) ° with the methoxyphenyl part. The hydroxy group forms an intramolecular hydrogen bond to the carbonyl oxygen atom of the fragment (Fig. 1).

Experimental

Kaempferia rotunda rhizomes were purchased from a market in Kempas, Johor. The rhizomes were dried and then grounded. The grounded rhizomes were extracted with n-hexane (4.5 L), ethyl acetate (4.5 L) and methanol (4.5 L) in a soxhlet extractor for 16 h. The extracts were concentrated to give a dark brown semi-solid from the n-hexane extract (2.32 g), a dark brown oil from the ethyl acetate extract (6.80 g) and a dark brown viscous liquid from the methanol extract (15.27 g). The n-hexane extract was purified by column chromatography (93.0 g, column size: 4.5 × 45.0 cm) with n-hexane:ether (99:1, 98:2 and 97:3) as eluents to give 20 fractions. Fractions 13 (0.08 g) and 14 (0.02 g) were combined and recrystallized by from an n-hexane: ether mixture to afford the title compound (6.9 mg) as yellow crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–15U(C).

The hydroxy H-atom was located in a difference Fourier map, and was refined isotropically with the O–H distance restrained to 0.84±0.01 Å.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C18H18O5 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H18O5F(000) = 664
Mr = 314.32Dx = 1.389 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5893 reflections
a = 12.8502 (8) Åθ = 2.3–28.2°
b = 8.3226 (5) ŵ = 0.10 mm1
c = 14.1865 (9) ÅT = 100 K
β = 97.765 (1)°Irregular block, yellow
V = 1503.29 (16) Å30.45 × 0.40 × 0.05 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer2989 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
graphiteθmax = 27.5°, θmin = 2.0°
ω scansh = −16→15
13992 measured reflectionsk = −10→10
3464 independent reflectionsl = −18→18

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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0545P)2 + 0.5468P] where P = (Fo2 + 2Fc2)/3
3464 reflections(Δ/σ)max = 0.001
215 parametersΔρmax = 0.32 e Å3
1 restraintΔρmin = −0.23 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.71889 (6)0.58291 (10)0.67517 (6)0.02051 (19)
H10.7343 (14)0.536 (2)0.6242 (9)0.049 (5)*
O20.44911 (7)0.93407 (10)0.74558 (6)0.0224 (2)
O30.45229 (6)0.75473 (10)0.42926 (5)0.01955 (19)
O40.72544 (6)0.50207 (10)0.50890 (6)0.02089 (19)
O50.61863 (7)0.54719 (10)−0.08390 (5)0.01985 (19)
C10.63266 (9)0.66965 (13)0.64416 (8)0.0166 (2)
C20.58866 (9)0.75693 (13)0.71251 (8)0.0181 (2)
H20.61990.75600.77710.022*
C30.49855 (9)0.84502 (13)0.68446 (8)0.0176 (2)
C40.45027 (9)0.84618 (14)0.58972 (8)0.0177 (2)
H40.38690.90410.57240.021*
C50.49567 (9)0.76227 (13)0.52174 (8)0.0163 (2)
C60.59130 (8)0.67424 (13)0.54579 (7)0.0160 (2)
C70.49545 (11)0.93606 (16)0.84345 (8)0.0257 (3)
H7A0.44870.99240.88150.039*
H7B0.56320.99170.84910.039*
H7C0.50610.82550.86650.039*
C80.35464 (9)0.83628 (15)0.40224 (8)0.0210 (2)
H8A0.33320.82360.33370.032*
H8B0.36320.95070.41760.032*
H8C0.30080.79030.43700.032*
C90.64968 (9)0.59271 (13)0.47819 (8)0.0170 (2)
C100.62915 (9)0.61886 (14)0.37466 (8)0.0180 (2)
H100.59140.71100.34970.022*
C110.66420 (9)0.51130 (14)0.31598 (8)0.0179 (2)
H110.69760.41820.34460.022*
C120.65630 (8)0.52262 (14)0.21240 (8)0.0170 (2)
C130.67036 (9)0.38511 (14)0.15961 (8)0.0194 (2)
H130.68800.28700.19220.023*
C140.65939 (9)0.38694 (14)0.06058 (8)0.0191 (2)
H140.66860.29120.02620.023*
C150.63480 (8)0.53098 (14)0.01267 (8)0.0166 (2)
C160.62576 (9)0.67210 (14)0.06464 (8)0.0192 (2)
H160.61270.77140.03220.023*
C170.63562 (9)0.66808 (14)0.16271 (8)0.0183 (2)
H170.62840.76450.19710.022*
C180.63148 (10)0.40641 (15)−0.13935 (8)0.0219 (2)
H18A0.61410.4319−0.20710.033*
H18B0.58470.3215−0.12220.033*
H18C0.70450.3696−0.12670.033*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0192 (4)0.0242 (4)0.0175 (4)0.0058 (3)0.0000 (3)0.0029 (3)
O20.0276 (5)0.0221 (4)0.0174 (4)0.0066 (3)0.0027 (3)−0.0003 (3)
O30.0168 (4)0.0253 (4)0.0156 (4)0.0041 (3)−0.0011 (3)0.0016 (3)
O40.0204 (4)0.0229 (4)0.0191 (4)0.0052 (3)0.0017 (3)0.0024 (3)
O50.0246 (4)0.0197 (4)0.0156 (4)0.0016 (3)0.0042 (3)0.0000 (3)
C10.0150 (5)0.0154 (5)0.0188 (5)−0.0015 (4)0.0007 (4)0.0041 (4)
C20.0200 (6)0.0183 (5)0.0152 (5)−0.0012 (4)−0.0001 (4)0.0025 (4)
C30.0200 (5)0.0147 (5)0.0185 (5)−0.0016 (4)0.0044 (4)0.0006 (4)
C40.0166 (5)0.0172 (5)0.0191 (5)0.0017 (4)0.0018 (4)0.0037 (4)
C50.0168 (5)0.0159 (5)0.0156 (5)−0.0025 (4)0.0002 (4)0.0032 (4)
C60.0160 (5)0.0157 (5)0.0160 (5)−0.0013 (4)0.0016 (4)0.0023 (4)
C70.0348 (7)0.0229 (6)0.0188 (6)0.0044 (5)0.0013 (5)−0.0027 (5)
C80.0170 (5)0.0242 (6)0.0207 (5)0.0033 (4)−0.0019 (4)0.0034 (4)
C90.0161 (5)0.0156 (5)0.0189 (5)−0.0026 (4)0.0013 (4)0.0021 (4)
C100.0162 (5)0.0194 (5)0.0184 (5)0.0002 (4)0.0023 (4)0.0038 (4)
C110.0173 (5)0.0180 (5)0.0181 (5)−0.0008 (4)0.0011 (4)0.0031 (4)
C120.0142 (5)0.0198 (6)0.0171 (5)0.0005 (4)0.0022 (4)0.0012 (4)
C130.0199 (6)0.0167 (5)0.0211 (6)0.0025 (4)0.0011 (4)0.0030 (4)
C140.0187 (5)0.0179 (6)0.0206 (5)0.0021 (4)0.0024 (4)−0.0014 (4)
C150.0131 (5)0.0210 (6)0.0160 (5)−0.0005 (4)0.0030 (4)0.0003 (4)
C160.0207 (6)0.0167 (5)0.0205 (5)0.0021 (4)0.0039 (4)0.0027 (4)
C170.0191 (5)0.0169 (6)0.0190 (5)0.0008 (4)0.0035 (4)−0.0005 (4)
C180.0253 (6)0.0220 (6)0.0193 (5)−0.0011 (5)0.0060 (4)−0.0033 (4)

Geometric parameters (Å, °)

O1—C11.3457 (13)C8—H8A0.9800
O1—H10.867 (9)C8—H8B0.9800
O2—C31.3615 (14)C8—H8C0.9800
O2—C71.4349 (14)C9—C101.4728 (15)
O3—C51.3558 (13)C10—C111.3411 (16)
O3—C81.4326 (13)C10—H100.9500
O4—C91.2618 (14)C11—C121.4623 (15)
O5—C151.3644 (13)C11—H110.9500
O5—C181.4331 (14)C12—C131.3927 (16)
C1—C21.3913 (16)C12—C171.4079 (16)
C1—C61.4250 (15)C13—C141.3929 (16)
C2—C31.3828 (16)C13—H130.9500
C2—H20.9500C14—C151.3932 (16)
C3—C41.4023 (15)C14—H140.9500
C4—C51.3820 (16)C15—C161.3999 (16)
C4—H40.9500C16—C171.3804 (16)
C5—C61.4318 (15)C16—H160.9500
C6—C91.4619 (15)C17—H170.9500
C7—H7A0.9800C18—H18A0.9800
C7—H7B0.9800C18—H18B0.9800
C7—H7C0.9800C18—H18C0.9800
C1—O1—H1103.7 (12)O4—C9—C6119.43 (10)
C3—O2—C7117.01 (9)O4—C9—C10117.29 (10)
C5—O3—C8117.88 (9)C6—C9—C10123.16 (10)
C15—O5—C18117.20 (9)C11—C10—C9119.37 (10)
O1—C1—C2116.51 (10)C11—C10—H10120.3
O1—C1—C6121.08 (10)C9—C10—H10120.3
C2—C1—C6122.39 (10)C10—C11—C12126.67 (10)
C3—C2—C1118.66 (10)C10—C11—H11116.7
C3—C2—H2120.7C12—C11—H11116.7
C1—C2—H2120.7C13—C12—C17117.82 (10)
O2—C3—C2123.37 (10)C13—C12—C11119.40 (10)
O2—C3—C4115.00 (10)C17—C12—C11122.77 (10)
C2—C3—C4121.63 (10)C12—C13—C14122.04 (10)
C5—C4—C3119.44 (10)C12—C13—H13119.0
C5—C4—H4120.3C14—C13—H13119.0
C3—C4—H4120.3C15—C14—C13119.13 (10)
O3—C5—C4122.78 (10)C15—C14—H14120.4
O3—C5—C6115.74 (10)C13—C14—H14120.4
C4—C5—C6121.46 (10)O5—C15—C14124.66 (10)
C1—C6—C5116.20 (10)O5—C15—C16115.70 (10)
C1—C6—C9118.26 (10)C14—C15—C16119.64 (10)
C5—C6—C9125.53 (10)C17—C16—C15120.50 (10)
O2—C7—H7A109.5C17—C16—H16119.7
O2—C7—H7B109.5C15—C16—H16119.7
H7A—C7—H7B109.5C16—C17—C12120.72 (10)
O2—C7—H7C109.5C16—C17—H17119.6
H7A—C7—H7C109.5C12—C17—H17119.6
H7B—C7—H7C109.5O5—C18—H18A109.5
O3—C8—H8A109.5O5—C18—H18B109.5
O3—C8—H8B109.5H18A—C18—H18B109.5
H8A—C8—H8B109.5O5—C18—H18C109.5
O3—C8—H8C109.5H18A—C18—H18C109.5
H8A—C8—H8C109.5H18B—C18—H18C109.5
H8B—C8—H8C109.5
O1—C1—C2—C3−178.53 (10)C5—C6—C9—O4−170.97 (10)
C6—C1—C2—C33.23 (17)C1—C6—C9—C10−165.63 (10)
C7—O2—C3—C20.85 (16)C5—C6—C9—C1013.18 (17)
C7—O2—C3—C4179.78 (10)O4—C9—C10—C1122.06 (16)
C1—C2—C3—O2179.81 (10)C6—C9—C10—C11−162.02 (11)
C1—C2—C3—C40.96 (17)C9—C10—C11—C12−176.23 (10)
O2—C3—C4—C5178.59 (10)C10—C11—C12—C13−162.90 (11)
C2—C3—C4—C5−2.46 (17)C10—C11—C12—C1717.58 (18)
C8—O3—C5—C4−0.74 (16)C17—C12—C13—C14−3.23 (17)
C8—O3—C5—C6177.90 (10)C11—C12—C13—C14177.23 (10)
C3—C4—C5—O3178.40 (10)C12—C13—C14—C150.76 (18)
C3—C4—C5—C6−0.17 (17)C18—O5—C15—C14−2.19 (16)
O1—C1—C6—C5176.25 (10)C18—O5—C15—C16177.52 (10)
C2—C1—C6—C5−5.59 (16)C13—C14—C15—O5−177.73 (10)
O1—C1—C6—C9−4.83 (16)C13—C14—C15—C162.57 (17)
C2—C1—C6—C9173.33 (10)O5—C15—C16—C17176.90 (10)
O3—C5—C6—C1−174.67 (9)C14—C15—C16—C17−3.38 (17)
C4—C5—C6—C14.00 (16)C15—C16—C17—C120.84 (17)
O3—C5—C6—C96.50 (16)C13—C12—C17—C162.41 (17)
C4—C5—C6—C9−174.84 (11)C11—C12—C17—C16−178.06 (11)
C1—C6—C9—O410.22 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O40.87 (1)1.65 (1)2.465 (1)156 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5385).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sirat, H. M., Jamil, S. & Siew, L. W. (2001). ACGC Chem. Res. Commun.13, 48–54.
  • Stevenson, P. C., Veitch, N. C. & Simmonds, M. S. J. (2007). Phytochemistry, 68, 1579–1586. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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