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Acta Cryst. (2010). E66, o2944    [ doi:10.1107/S1600536810042674 ]

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

H. M. Sirat, Y. S. Feng, H. Hazni, K. Awang and S. W. Ng

Abstract top

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.

Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C18H18O5 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
(E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one top
Crystal data top
C18H18O5F(000) = 664
Mr = 314.32Dx = 1.389 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		2989 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 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 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 Å−3
1 restraintΔρmin = −0.23 e Å−3
Crystal data top
C18H18O5V = 1503.29 (16) Å3
Mr = 314.32Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.8502 (8) ŵ = 0.10 mm−1
b = 8.3226 (5) ÅT = 100 K
c = 14.1865 (9) Å0.45 × 0.40 × 0.05 mm
β = 97.765 (1)°
Data collection top
Bruker SMART APEX
diffractometer		2989 reflections with I > 2σ(I)
13992 measured reflectionsRint = 0.027
3464 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101Δρmax = 0.32 e Å−3
S = 1.01Δρmin = −0.23 e Å−3
3464 reflectionsAbsolute structure: ?
215 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.87 (1)1.65 (1)2.465 (1)156 (2)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.87 (1)1.65 (1)2.465 (1)156 (2)
Acknowledgements top

We thank the University of Malaya for supporting this study.

references
References top

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Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

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Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.