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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2866
https://doi.org/10.1107/S1600536810041395

Flavokavain B from the rhizome of Alpinia mutica Roxb

Hasnah Mohd Sirat,a Nor Akmalazura Jani,a Hazrina Hazni,b Khalijah Awangb and Seik Weng Ngb*

aDepartment of Chemistry, Universiti Teknologi Malaysia, 81310 Skudai, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 23 September 2010; accepted 14 October 2010; online 20 October 2010)

The title compound [systematic name: (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one], C17H16O4, has an aromatic ring at both ends of the –CH= CH–C(=O)– fragment with the –CH=CH– bond in a trans configuration. The phenyl ring is nearly coplanar with this fragment [dihedral angle 4.8 (3) °] as is the hy­droxy­ldimeth­oxy­lphenyl unit [dihedral angle 6.3 (3) °]. The hy­droxy group is the donor in an intra­molecular hydrogen bond to the double-bonded O atom.

Related literature

For the isolation and spectroscopic characterization of the title compound, see: Flores et al. (2007[Flores, N., Cabrera, G., Jimenez, I. A., Pinero, J., Gimenez, A., Bourdy, G., Cortes-Selva, F. & Bazzocchi, I. (2007). Planta Med. 73, 206-211.]); Xuan et al. (2008[Xuan, T. D., Fukuta, M., Wei, A. C., Elzaawely, A. A., Khanh, T. D. & Tawata, S. (2008). J. Nat. Med. 62, 188-194.]).

[Scheme 1]

Experimental

Crystal data

  • C17H16O4

  • Mr = 284.30

  • Orthorhombic, P 21 21 21

  • a = 4.9668 (10) Å

  • b = 12.305 (3) Å

  • c = 22.552 (5) Å

  • V = 1378.3 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 100 K

  • 0.40 × 0.10 × 0.05 mm
Data collection

  • Bruker SMART APEX diffractometer

  • 10723 measured reflections

  • 1449 independent reflections

  • 1162 reflections with I > 2σ(I)

  • Rint = 0.089
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.128

  • S = 1.09

  • 1449 reflections

  • 197 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯O1 0.85 (1) 1.65 (2) 2.455 (4) 157 (4)

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810041395/fl2321sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041395/fl2321Isup2.hkl

checkCIF report


Comment top

Alpinia mutica is a perennial herb (Zingiberaceae) endemic to southern parts of Malaysia. It is also cultivated as an ornamental plant and the rhizomes are used as an herb for strengthening the stomach. Among the compounds isolated this herb is Flavokavain B, whose structure was elucidated by spectrospic methods (Flores et al., 2007; Xuan et al., 2008) and whose x-ray structure is reported here. The chalcone (Scheme I) has aromatic rings at either ends of the –CH═ CH–C(═O)– linkage; the -CH=CH- double bond has a trans configuration. The phenyl ring is nearly coplanar with this fragment [dihedral angle 4.8 (3) °] as is the hydroxyldimethoxylphenyl ring [dihderal angle 6.3 (3) ° (the dihedral angle between the two rings is 10.0 (2)°) (Fig. 1). The hydroxy group is donor in an intra-molecular H-bond bond with the double-bond oxygen atom of the fragment. Other than a close contact of 3.04 Å between O2 and C16, there are no important intermolecular contacts (Fig. 2).

The compound has been previously isolated and characterized by NMR spectroscopy (Flores et al., 2007; Xuan et al., 2008).

Related literature top

For the isolation and spectroscopic characterization, see: Flores et al. (2007); Xuan et al. (2008).

Experimental top

The rhizome of Alpinia mutica was collected from Pontian, Johor, Malaysia. A voucher specimen was deposited at the Herbarium of the Departmentof Botany, Universiti Putra Malaysia. The n-hexane crude extract of the rhizome (8.97 g) was subjected to silica-gel chromatography and was eluted out by using a gradient mixture of petroleum ether, ethanol and methanol. Twenty three fractions were collected, which were then separated by TLC to afford eight fractions. The sixth fraction was subjected to silica-gel column chromatography to give the title compound (petroleum ether: ether 4/1)which was recrystallized from petroleum ether/ether to afford faint yellow-orange crystals suitable for data collection.

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 with the O–H distance restrained to 0.84±0.01 Å; its temperature factor was refined.

In the absence of heavy atom, Some 976 Friedel pairs were merged.

Structure description top

Alpinia mutica is a perennial herb (Zingiberaceae) endemic to southern parts of Malaysia. It is also cultivated as an ornamental plant and the rhizomes are used as an herb for strengthening the stomach. Among the compounds isolated this herb is Flavokavain B, whose structure was elucidated by spectrospic methods (Flores et al., 2007; Xuan et al., 2008) and whose x-ray structure is reported here. The chalcone (Scheme I) has aromatic rings at either ends of the –CH═ CH–C(═O)– linkage; the -CH=CH- double bond has a trans configuration. The phenyl ring is nearly coplanar with this fragment [dihedral angle 4.8 (3) °] as is the hydroxyldimethoxylphenyl ring [dihderal angle 6.3 (3) ° (the dihedral angle between the two rings is 10.0 (2)°) (Fig. 1). The hydroxy group is donor in an intra-molecular H-bond bond with the double-bond oxygen atom of the fragment. Other than a close contact of 3.04 Å between O2 and C16, there are no important intermolecular contacts (Fig. 2).

The compound has been previously isolated and characterized by NMR spectroscopy (Flores et al., 2007; Xuan et al., 2008).

For the isolation and spectroscopic characterization, see: Flores et al. (2007); Xuan et al. (2008).

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. Thermal ellipsoid plot (Barbour, 2001) of the C17H16O4 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. Close approach of ajacent molecules.
(E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one top
Crystal data top
C17H16O4F(000) = 600
Mr = 284.30Dx = 1.370 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1135 reflections
a = 4.9668 (10) Åθ = 3.2–21.7°
b = 12.305 (3) ŵ = 0.10 mm−1
c = 22.552 (5) ÅT = 100 K
V = 1378.3 (5) Å3Prism, faint yellow
Z = 40.40 × 0.10 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		1162 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.089
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω scansh = −5→5
10723 measured reflectionsk = −14→14
1449 independent reflectionsl = −26→25
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0736P)2 + 0.021P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
1449 reflectionsΔρmax = 0.20 e Å−3
197 parametersΔρmin = −0.27 e Å−3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (5)
Crystal data top
C17H16O4V = 1378.3 (5) Å3
Mr = 284.30Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.9668 (10) ŵ = 0.10 mm−1
b = 12.305 (3) ÅT = 100 K
c = 22.552 (5) Å0.40 × 0.10 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		1162 reflections with I > 2σ(I)
10723 measured reflectionsRint = 0.089
1449 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.20 e Å−3
1449 reflectionsΔρmin = −0.27 e Å−3
197 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5688 (6)0.96830 (19)0.22125 (11)0.0250 (7)
O20.3291 (6)0.9379 (2)0.12751 (11)0.0260 (7)
H20.440 (7)0.958 (4)0.1541 (14)0.048 (15)*
O3−0.3912 (5)0.68445 (19)0.12028 (10)0.0245 (7)
O40.0995 (6)0.72577 (18)0.29718 (11)0.0272 (7)
C10.7327 (8)0.9257 (3)0.40417 (17)0.0228 (9)
C20.5796 (9)0.8616 (3)0.44201 (16)0.0283 (10)
H2A0.43690.81910.42620.034*
C30.6311 (10)0.8586 (3)0.50210 (18)0.0349 (10)
H30.52300.81500.52740.042*
C40.8406 (9)0.9191 (3)0.52537 (17)0.0323 (11)
H40.87620.91770.56680.039*
C50.9976 (9)0.9815 (3)0.48823 (18)0.0310 (10)
H51.14181.02290.50420.037*
C60.9476 (9)0.9846 (3)0.42798 (17)0.0279 (10)
H61.05941.02670.40270.034*
C70.6751 (8)0.9328 (3)0.34039 (17)0.0257 (9)
H70.79940.97230.31670.031*
C80.4658 (8)0.8891 (3)0.31275 (16)0.0256 (9)
H80.33810.84930.33540.031*
C90.4237 (8)0.8998 (3)0.24859 (16)0.0230 (9)
C100.2169 (8)0.8393 (3)0.21647 (16)0.0196 (8)
C110.1737 (8)0.8639 (3)0.15591 (16)0.0208 (9)
C12−0.0285 (8)0.8174 (3)0.12220 (16)0.0230 (9)
H12−0.05860.83920.08230.028*
C13−0.1857 (8)0.7377 (3)0.14850 (16)0.0213 (9)
C14−0.1454 (8)0.7058 (3)0.20702 (16)0.0221 (8)
H14−0.25440.65040.22380.027*
C150.0513 (8)0.7543 (3)0.24038 (15)0.0211 (9)
C16−0.0619 (9)0.6404 (3)0.32205 (16)0.0298 (10)
H16A−0.01150.62920.36360.045*
H16B−0.03200.57310.29980.045*
H16C−0.25250.66060.31970.045*
C17−0.4398 (9)0.7113 (3)0.05989 (15)0.0287 (10)
H17A−0.59070.66790.04490.043*
H17B−0.27830.69570.03640.043*
H17C−0.48390.78870.05670.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0269 (15)0.0177 (12)0.0304 (15)−0.0032 (12)0.0027 (13)0.0014 (11)
O20.0313 (17)0.0199 (13)0.0266 (16)−0.0038 (13)0.0000 (14)0.0034 (12)
O30.0254 (15)0.0218 (13)0.0263 (14)−0.0010 (12)−0.0042 (13)−0.0008 (11)
O40.0393 (17)0.0180 (12)0.0243 (14)−0.0075 (13)−0.0017 (13)0.0058 (11)
C10.026 (2)0.0154 (19)0.027 (2)0.0059 (17)−0.0030 (18)−0.0031 (16)
C20.031 (2)0.0254 (19)0.028 (2)−0.006 (2)−0.002 (2)−0.0019 (17)
C30.038 (3)0.037 (2)0.030 (2)−0.006 (2)0.001 (2)0.0001 (19)
C40.044 (3)0.026 (2)0.027 (2)0.001 (2)−0.006 (2)0.0006 (17)
C50.035 (3)0.021 (2)0.037 (2)−0.0020 (19)−0.006 (2)−0.0040 (17)
C60.032 (2)0.0211 (19)0.031 (2)−0.0026 (19)−0.0017 (19)0.0021 (17)
C70.028 (2)0.0173 (18)0.032 (2)−0.0015 (18)0.005 (2)0.0007 (17)
C80.030 (2)0.0205 (19)0.026 (2)−0.0034 (17)−0.0005 (19)−0.0006 (16)
C90.024 (2)0.0154 (16)0.029 (2)0.0021 (17)0.0054 (19)−0.0024 (16)
C100.022 (2)0.0140 (17)0.023 (2)0.0009 (15)0.0026 (17)−0.0038 (15)
C110.025 (2)0.0115 (17)0.025 (2)0.0016 (16)0.0052 (18)0.0015 (15)
C120.030 (2)0.0202 (19)0.0191 (19)0.0022 (17)−0.0020 (18)−0.0002 (15)
C130.024 (2)0.0159 (17)0.025 (2)0.0029 (16)−0.0010 (17)−0.0036 (15)
C140.022 (2)0.0158 (16)0.029 (2)0.0009 (16)0.0002 (18)0.0005 (15)
C150.030 (2)0.0139 (16)0.0197 (18)0.0015 (16)0.0000 (18)−0.0011 (14)
C160.043 (3)0.0207 (18)0.026 (2)−0.0075 (19)−0.002 (2)0.0089 (16)
C170.036 (3)0.027 (2)0.024 (2)−0.001 (2)−0.001 (2)−0.0043 (16)
Geometric parameters (Å, º) top
O1—C91.269 (4)C7—C81.326 (5)
O2—C111.354 (4)C7—H70.9500
O2—H20.85 (1)C8—C91.468 (5)
O3—C131.370 (5)C8—H80.9500
O3—C171.422 (4)C9—C101.461 (5)
O4—C151.349 (4)C10—C111.415 (5)
O4—C161.436 (4)C10—C151.436 (5)
C1—C21.389 (5)C11—C121.384 (5)
C1—C61.397 (5)C12—C131.386 (5)
C1—C71.469 (5)C12—H120.9500
C2—C31.380 (5)C13—C141.391 (5)
C2—H2A0.9500C14—C151.370 (5)
C3—C41.383 (6)C14—H140.9500
C3—H30.9500C16—H16A0.9800
C4—C51.378 (6)C16—H16B0.9800
C4—H40.9500C16—H16C0.9800
C5—C61.382 (5)C17—H17A0.9800
C5—H50.9500C17—H17B0.9800
C6—H60.9500C17—H17C0.9800
C11—O2—H2103 (3)C11—C10—C15115.5 (3)
C13—O3—C17117.4 (3)C11—C10—C9118.4 (3)
C15—O4—C16117.5 (3)C15—C10—C9126.0 (3)
C2—C1—C6118.5 (4)O2—C11—C12115.6 (3)
C2—C1—C7121.9 (4)O2—C11—C10120.9 (4)
C6—C1—C7119.6 (4)C12—C11—C10123.5 (3)
C3—C2—C1121.1 (4)C11—C12—C13117.8 (3)
C3—C2—H2A119.4C11—C12—H12121.1
C1—C2—H2A119.4C13—C12—H12121.1
C2—C3—C4119.8 (4)O3—C13—C12124.0 (3)
C2—C3—H3120.1O3—C13—C14114.4 (3)
C4—C3—H3120.1C12—C13—C14121.6 (4)
C5—C4—C3119.7 (4)C15—C14—C13120.0 (4)
C5—C4—H4120.2C15—C14—H14120.0
C3—C4—H4120.2C13—C14—H14120.0
C4—C5—C6120.7 (4)O4—C15—C14122.3 (3)
C4—C5—H5119.6O4—C15—C10116.4 (3)
C6—C5—H5119.6C14—C15—C10121.3 (3)
C5—C6—C1120.1 (4)O4—C16—H16A109.5
C5—C6—H6120.0O4—C16—H16B109.5
C1—C6—H6120.0H16A—C16—H16B109.5
C8—C7—C1126.1 (4)O4—C16—H16C109.5
C8—C7—H7117.0H16A—C16—H16C109.5
C1—C7—H7117.0H16B—C16—H16C109.5
C7—C8—C9122.6 (4)O3—C17—H17A109.5
C7—C8—H8118.7O3—C17—H17B109.5
C9—C8—H8118.7H17A—C17—H17B109.5
O1—C9—C10119.8 (3)O3—C17—H17C109.5
O1—C9—C8117.2 (4)H17A—C17—H17C109.5
C10—C9—C8122.9 (3)H17B—C17—H17C109.5
C6—C1—C2—C32.3 (6)C15—C10—C11—C125.5 (5)
C7—C1—C2—C3−177.9 (4)C9—C10—C11—C12−175.4 (3)
C1—C2—C3—C4−0.8 (6)O2—C11—C12—C13177.2 (3)
C2—C3—C4—C5−0.4 (6)C10—C11—C12—C13−4.0 (5)
C3—C4—C5—C60.2 (6)C17—O3—C13—C121.6 (5)
C4—C5—C6—C11.3 (6)C17—O3—C13—C14−178.6 (3)
C2—C1—C6—C5−2.5 (6)C11—C12—C13—O3−179.6 (3)
C7—C1—C6—C5177.7 (4)C11—C12—C13—C140.7 (5)
C2—C1—C7—C86.2 (6)O3—C13—C14—C15−178.9 (3)
C6—C1—C7—C8−173.9 (4)C12—C13—C14—C150.8 (6)
C1—C7—C8—C9−179.8 (4)C16—O4—C15—C140.8 (5)
C7—C8—C9—O1−12.0 (5)C16—O4—C15—C10−179.6 (3)
C7—C8—C9—C10170.8 (4)C13—C14—C15—O4−179.6 (3)
O1—C9—C10—C11−3.8 (5)C13—C14—C15—C100.9 (6)
C8—C9—C10—C11173.4 (3)C11—C10—C15—O4176.6 (3)
O1—C9—C10—C15175.3 (3)C9—C10—C15—O4−2.5 (5)
C8—C9—C10—C15−7.5 (6)C11—C10—C15—C14−3.8 (5)
C15—C10—C11—O2−175.9 (3)C9—C10—C15—C14177.1 (4)
C9—C10—C11—O23.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.85 (1)1.65 (2)2.455 (4)157 (4)

Experimental details

Crystal data
Chemical formulaC17H16O4
Mr284.30
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)4.9668 (10), 12.305 (3), 22.552 (5)
V (Å3)1378.3 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.40 × 0.10 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		10723, 1449, 1162
Rint0.089
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.128, 1.09
No. of reflections1449
No. of parameters197
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.27

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O10.85 (1)1.65 (2)2.455 (4)157 (4)
 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFlores, N., Cabrera, G., Jimenez, I. A., Pinero, J., Gimenez, A., Bourdy, G., Cortes-Selva, F. & Bazzocchi, I. (2007). Planta Med. 73, 206–211.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXuan, T. D., Fukuta, M., Wei, A. C., Elzaawely, A. A., Khanh, T. D. & Tawata, S. (2008). J. Nat. Med. 62, 188–194.  Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2866
https://doi.org/10.1107/S1600536810041395
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