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

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ISSN: 2056-9890

1-(2,6-Dihydr­­oxy-4-meth­oxy­phen­yl)-3-phenyl­propan-1-one1

aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, bDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science and Technology, Suratthani Rajabhat University, Mueang, Surat Thani 84100, Thailand, cNatural Products Research Laboratory, School of Science, Mae Fah Luang University, Muang, Chiang Rai 57100, Thailand, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: suchada.c@psu.ac.th

(Received 2 April 2010; accepted 13 April 2010; online 21 April 2010)

The title compound, C16H16O4, a dihydro­chalcone, was isolated from the rhizomes of Etlingera littoralis. The mol­ecule is twisted with a dihedral angle of 71.69 (6)° between the two aromatic rings. The propanone unit makes dihedral angles of 4.07 (6) and 73.56 (7)°, respectively, with the 2,6-dihydroxy-4-methoxyphenyl and phenyl rings. The meth­oxy group is approximately coplanar with the attached benzene ring with a dihedral angle of 1.74 (10)°. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains along [201]. A ππ inter­action with a centroid–centroid distance of 3.5185 (6) Å is also observed.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background to dihydro­chalcones and their activities, see: Nilsson (1961[Nilsson, M. (1961). Acta Chem. Scand. 15, 154-158.]); Nowakowska (2007[Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.]); Portet et al. (2007[Portet, B., Fabre, N., Roumy, V., Gornitzka, H., Bourdy, G., Chevalley, S., Sauvain, M., Valentin, A. & Moulis, C. (2007). Phytochemistry, 68, 1312-1320.]). For Zingiberaceae plants, see: Chuakul & Boonpleng (2003[Chuakul, W. & Boonpleng, A. (2003). J. Med. Plants, 10, 33-35.]); Reanmongkol et al. (2006[Reanmongkol, W., Subhadhirasakul, S., Khaisombat, N., Fuengnawakit, P., Jantasila, S. & Khamjun, A. (2006). Songklanakarin J. Sci. Technol. 25, 999-1008.]); Sirirugsa (1999[Sirirugsa, P. (1999). Thai Zingiberaceae: Species diversity and their uses, http://www.iupac.org/symposia/proceedings/phuket97/sirirugsa.html.]); Tewtrakul, Subhadhirasakul & Kummee (2003[Tewtrakul, S., Subhadhirasakul, S. & Kummee, S. (2003). Songklanakarin J. Sci. Technol. 25, 239-243.]); Tewtrakul, Subhadhirasakul, Puripattanavong & Panphadung (2003[Tewtrakul, S., Subhadhirasakul, S., Puripattanavong, J. & Panphadung, T. (2003). Songklanakarin J. Sci. Technol. 25, 503-508.]). For a related structure, see: Ng et al. (2005[Ng, S.-L., Razak, I. A., Fun, H.-K., Boonsri, S., Chantrapromma, S. & Prawat, U. (2005). Acta Cryst. E61, o3234-o3236.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16O4

  • Mr = 272.29

  • Monoclinic, C c

  • a = 7.2142 (6) Å

  • b = 30.522 (2) Å

  • c = 6.5587 (5) Å

  • β = 107.267 (2)°

  • V = 1379.09 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 100 K

  • 0.46 × 0.34 × 0.18 mm

Data collection
  • Bruker APEX DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.983

  • 17744 measured reflections

  • 3044 independent reflections

  • 2940 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.097

  • S = 1.08

  • 3044 reflections

  • 186 parameters

  • 2 restraints

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

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H1O2⋯O1 0.82 1.71 2.4576 (11) 150
O4—H1O4⋯O2i 0.80 (3) 1.90 (3) 2.6920 (10) 175 (3)
Symmetry code: (i) [x+1, -y, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Zingiberaceae plants are the ground plants of tropical forests. Many of them are used for food, spices, medicines, dyes, perfume and aesthetics (Sirirugsa, 1999). Secondary metabolites from Zingiberaceae plants have found to be anti-inflammatory (Reanmongkol et al., 2006), HIV-1 protease inhibitory (Tewtrakul, Subhadhirasakul & Kummee, 2003; Tewtrakul, Subhadhirasakul, Puripattanavong & Panphadung, 2003). Etlingera littoralis is one of the Zingiberaceae plants and its decoction of the rhizomes has been used for the treatment of stomachache, carminative and heart tonic (Chuakul & Boonpleng, 2003). As part of our study of chemical constituents and bioactive compounds from the rhizomes of Etlingera littoralis which were collected from Surat Thani province in the southern of Thailand, the title dihydrochalcone, (I), was isolated. Herein we report its crystal structure. The title compound was found to possess antibacterial (Nowakowska, 2007) and antiplasmodial activities (Portet et al., 2007).

The molecule of the title dihydrochalcone (Fig. 1), C16H16O4, is twisted as the dihedral angle between the 2,6-dihydroxy-4-methoxyphenyl and phenyl rings is 71.69 (6)°. Whereas the 1-propanone unit (C7–C9/O1) makes the dihedral angles of 4.07 (6) and 73.56 (7)° with the C1–C6 benzene and C10–C15 phenyl rings, respectively. The two hydroxy and a methoxy groups are co-planar with the attached benzene ring with the r.m.s. of 0.0078 (1) Å for the ten non H atoms and the torsion angle C16–O3–C3–C2 = -1.66 (15)°. An intramolecular O2—H1O2···O1 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995) (Fig. 1 and Table 1). The bond distances are of normal values (Allen et al., 1987) and are comparable with the closely related structure (Ng et al., 2005).

In the crystal packing (Fig. 2) , O—H···O hydrogen bonds (Table 1) formed between the two hydroxy groups link the molecules into chains along the [201] direction in which the adjacent chains are in anti-parallel manner. A ππ interaction with Cg1···Cg1 distance of 3.5185 (6) Å was observed (symmetry code x, -y, -1/2+z); Cg1 is the centroid of the C1–C6 benzene ring.

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For background to dihydrochalcones and their activities, see: Nilsson (1961); Nowakowska (2007); Portet et al. (2007). For Zingiberaceae plants, see: Chuakul & Boonpleng (2003); Reanmongkol et al. (2006); Sirirugsa (1999); Tewtrakul, Subhadhirasakul & Kummee (2003); Tewtrakul, Subhadhirasakul, Puripattanavong & Panphadung (2003). For a related structure, see: Ng et al. (2005). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The fresh rhizomes of E. littoralis (3.89 kg) were chopped and extracted with 50% CH2Cl2-MeOH, over the period of 3 days at room temperature. The extraction was filtered and evaporated to dryness under reduced pressure to give crude extract which was further partitioned with water and CH2Cl2 to afford the dichloromethane extract (22.88 g). The portion of dichloromethane extract (11.80 g) was subjected to quick column chromatography (QCC) on silica gel eluting with a gradient of EtOAc–hexane to give thirteen fractions. Fraction F8 (322.4 mg) was washed with 20% CH2Cl2-hexane yielding solid which was further separated by column chromatography on silica gel with 70% CH2Cl2-hexane to give compound (I) (50.1 mg). Yellow block-shaped single crystals of the compound (I) suitable for X-ray structure determination were obtained from ethyl acetate by slow evaporation at room temperature after a few days, Mp 443 K. The NMR spectral data were consistent with the X-ray structure.

Refinement top

Hydroxy H atoms attached to O4 was located from a difference map and isotropically refined. The remaining H atoms were placed in calculated positions, with d(O—H) = 0.82 Å and d(C—H) = 0.93 Å for aromatic, 0.97 for CH2 and 0.96 Å for CH3 atoms. The Uiso(H) values were constrained to be 1.5Ueq of the carrier atom for hydroxy and methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual electron densitypeak is located at 0.69 Å from C1 and the deepest hole is located at 0.84 Å from C7. A total of 2607 Friedel pairs were merged before final refinement as there is no large anomalous dispersion for the determination of the absolute configuration.

Structure description top

Zingiberaceae plants are the ground plants of tropical forests. Many of them are used for food, spices, medicines, dyes, perfume and aesthetics (Sirirugsa, 1999). Secondary metabolites from Zingiberaceae plants have found to be anti-inflammatory (Reanmongkol et al., 2006), HIV-1 protease inhibitory (Tewtrakul, Subhadhirasakul & Kummee, 2003; Tewtrakul, Subhadhirasakul, Puripattanavong & Panphadung, 2003). Etlingera littoralis is one of the Zingiberaceae plants and its decoction of the rhizomes has been used for the treatment of stomachache, carminative and heart tonic (Chuakul & Boonpleng, 2003). As part of our study of chemical constituents and bioactive compounds from the rhizomes of Etlingera littoralis which were collected from Surat Thani province in the southern of Thailand, the title dihydrochalcone, (I), was isolated. Herein we report its crystal structure. The title compound was found to possess antibacterial (Nowakowska, 2007) and antiplasmodial activities (Portet et al., 2007).

The molecule of the title dihydrochalcone (Fig. 1), C16H16O4, is twisted as the dihedral angle between the 2,6-dihydroxy-4-methoxyphenyl and phenyl rings is 71.69 (6)°. Whereas the 1-propanone unit (C7–C9/O1) makes the dihedral angles of 4.07 (6) and 73.56 (7)° with the C1–C6 benzene and C10–C15 phenyl rings, respectively. The two hydroxy and a methoxy groups are co-planar with the attached benzene ring with the r.m.s. of 0.0078 (1) Å for the ten non H atoms and the torsion angle C16–O3–C3–C2 = -1.66 (15)°. An intramolecular O2—H1O2···O1 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995) (Fig. 1 and Table 1). The bond distances are of normal values (Allen et al., 1987) and are comparable with the closely related structure (Ng et al., 2005).

In the crystal packing (Fig. 2) , O—H···O hydrogen bonds (Table 1) formed between the two hydroxy groups link the molecules into chains along the [201] direction in which the adjacent chains are in anti-parallel manner. A ππ interaction with Cg1···Cg1 distance of 3.5185 (6) Å was observed (symmetry code x, -y, -1/2+z); Cg1 is the centroid of the C1–C6 benzene ring.

For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For background to dihydrochalcones and their activities, see: Nilsson (1961); Nowakowska (2007); Portet et al. (2007). For Zingiberaceae plants, see: Chuakul & Boonpleng (2003); Reanmongkol et al. (2006); Sirirugsa (1999); Tewtrakul, Subhadhirasakul & Kummee (2003); Tewtrakul, Subhadhirasakul, Puripattanavong & Panphadung (2003). For a related structure, see: Ng et al. (2005). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed down the b axis, showing chains running along the [201] direction. Hydrogen bonds are shown as dashed lines.
1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one top
Crystal data top
C16H16O4F(000) = 576
Mr = 272.29Dx = 1.311 Mg m3
Monoclinic, CcMelting point: 443 K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 7.2142 (6) ÅCell parameters from 3044 reflections
b = 30.522 (2) Åθ = 2.7–35.0°
c = 6.5587 (5) ŵ = 0.09 mm1
β = 107.267 (2)°T = 100 K
V = 1379.09 (18) Å3Block, yellow
Z = 40.46 × 0.34 × 0.18 mm
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
3044 independent reflections
Radiation source: sealed tube2940 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
φ and ω scansθmax = 35.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1111
Tmin = 0.958, Tmax = 0.983k = 4948
17744 measured reflectionsl = 1010
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0648P)2 + 0.1812P]
where P = (Fo2 + 2Fc2)/3
3044 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 0.34 e Å3
2 restraintsΔρmin = 0.40 e Å3
Crystal data top
C16H16O4V = 1379.09 (18) Å3
Mr = 272.29Z = 4
Monoclinic, CcMo Kα radiation
a = 7.2142 (6) ŵ = 0.09 mm1
b = 30.522 (2) ÅT = 100 K
c = 6.5587 (5) Å0.46 × 0.34 × 0.18 mm
β = 107.267 (2)°
Data collection top
Bruker APEX DUO CCD area-detector
diffractometer
3044 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
2940 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.983Rint = 0.025
17744 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0342 restraints
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.34 e Å3
3044 reflectionsΔρmin = 0.40 e Å3
186 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O10.57929 (10)0.09273 (3)0.16110 (12)0.01772 (14)
O20.40256 (10)0.02283 (2)0.09183 (12)0.01659 (14)
H1O20.42120.04940.09970.025*
O30.76008 (12)0.11076 (2)0.22402 (13)0.01827 (13)
O41.09458 (10)0.02313 (2)0.35682 (12)0.01540 (13)
H1O41.186 (4)0.0088 (8)0.419 (4)0.043 (6)*
C10.57479 (11)0.00170 (3)0.15654 (13)0.01230 (14)
C20.56979 (13)0.04392 (3)0.15433 (14)0.01400 (15)
H2A0.45240.05890.11020.017*
C30.74533 (14)0.06642 (3)0.21997 (15)0.01307 (13)
C40.92225 (13)0.04409 (3)0.28721 (14)0.01272 (14)
H4A1.03810.05970.32980.015*
C50.92521 (11)0.00137 (3)0.29051 (12)0.01140 (13)
C60.75073 (14)0.02604 (3)0.22318 (15)0.01112 (13)
C70.74075 (13)0.07385 (3)0.21838 (14)0.01271 (13)
C80.91965 (13)0.10221 (3)0.27702 (14)0.01421 (14)
H8A1.00230.09360.19110.017*
H8B0.99110.09710.42550.017*
C90.87479 (16)0.15107 (3)0.24454 (17)0.01880 (16)
H9A0.78930.15590.10130.023*
H9B0.80810.16080.34480.023*
C101.05757 (16)0.17743 (3)0.27659 (18)0.01983 (18)
C111.1302 (2)0.20381 (4)0.4562 (2)0.0303 (2)
H11A1.06620.20490.56010.036*
C121.2988 (3)0.22868 (4)0.4815 (3)0.0440 (4)
H12A1.34550.24630.60130.053*
C131.3961 (2)0.22708 (5)0.3287 (3)0.0453 (4)
H13A1.50740.24380.34550.054*
C141.3276 (2)0.20066 (5)0.1517 (3)0.0396 (3)
H14A1.39380.19920.04990.048*
C151.15876 (19)0.17616 (4)0.1255 (2)0.0273 (2)
H15A1.11280.15870.00490.033*
C160.58350 (17)0.13568 (3)0.16199 (18)0.0230 (2)
H16A0.61360.16640.17750.034*
H16B0.51420.12940.01570.034*
H16C0.50460.12790.25130.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0124 (3)0.0166 (3)0.0227 (3)0.0027 (2)0.0030 (2)0.0000 (3)
O20.0085 (3)0.0182 (3)0.0212 (3)0.0004 (2)0.0016 (2)0.0017 (2)
O30.0201 (3)0.0120 (3)0.0216 (3)0.0026 (2)0.0044 (2)0.0005 (2)
O40.0072 (2)0.0147 (3)0.0221 (3)0.0008 (2)0.0010 (2)0.0007 (2)
C10.0087 (3)0.0161 (3)0.0118 (3)0.0003 (3)0.0025 (2)0.0004 (3)
C20.0119 (3)0.0157 (3)0.0139 (3)0.0030 (3)0.0030 (3)0.0011 (3)
C30.0144 (3)0.0129 (3)0.0116 (3)0.0014 (3)0.0034 (2)0.0004 (3)
C40.0111 (3)0.0132 (3)0.0134 (3)0.0002 (3)0.0029 (2)0.0002 (3)
C50.0089 (3)0.0135 (3)0.0114 (3)0.0005 (3)0.0025 (2)0.0002 (3)
C60.0087 (3)0.0128 (3)0.0114 (3)0.0007 (3)0.0022 (2)0.0004 (3)
C70.0117 (3)0.0137 (3)0.0124 (3)0.0003 (3)0.0032 (2)0.0002 (3)
C80.0130 (3)0.0125 (3)0.0161 (3)0.0013 (3)0.0028 (3)0.0007 (3)
C90.0179 (4)0.0126 (3)0.0242 (4)0.0011 (3)0.0036 (3)0.0009 (3)
C100.0203 (4)0.0112 (3)0.0232 (4)0.0016 (3)0.0010 (3)0.0012 (3)
C110.0361 (6)0.0168 (4)0.0293 (5)0.0027 (4)0.0035 (4)0.0040 (4)
C120.0459 (8)0.0190 (5)0.0472 (8)0.0115 (5)0.0170 (6)0.0002 (5)
C130.0297 (6)0.0271 (6)0.0637 (10)0.0136 (5)0.0098 (6)0.0190 (6)
C140.0266 (5)0.0360 (7)0.0532 (8)0.0074 (5)0.0073 (6)0.0202 (6)
C150.0251 (5)0.0238 (5)0.0308 (5)0.0043 (4)0.0052 (4)0.0054 (4)
C160.0263 (5)0.0178 (4)0.0227 (4)0.0090 (4)0.0040 (4)0.0014 (3)
Geometric parameters (Å, º) top
O1—C71.2531 (11)C8—H8B0.9700
O2—C11.3516 (11)C9—C101.5052 (14)
O2—H1O20.8200C9—H9A0.9700
O3—C31.3574 (11)C9—H9B0.9700
O3—C161.4349 (13)C10—C111.3943 (15)
O4—C51.3445 (10)C10—C151.3951 (17)
O4—H1O40.79 (3)C11—C121.401 (2)
C1—C21.3928 (13)C11—H11A0.9300
C1—C61.4230 (12)C12—C131.384 (3)
C2—C31.3917 (14)C12—H12A0.9300
C2—H2A0.9300C13—C141.379 (3)
C3—C41.3978 (13)C13—H13A0.9300
C4—C51.3877 (12)C14—C151.3956 (18)
C4—H4A0.9300C14—H14A0.9300
C5—C61.4201 (12)C15—H15A0.9300
C6—C71.4607 (11)C16—H16A0.9600
C7—C81.5061 (13)C16—H16B0.9600
C8—C91.5276 (13)C16—H16C0.9600
C8—H8A0.9700
C1—O2—H1O2109.5C10—C9—C8111.21 (8)
C3—O3—C16117.72 (9)C10—C9—H9A109.4
C5—O4—H1O4115.4 (18)C8—C9—H9A109.4
O2—C1—C2117.08 (8)C10—C9—H9B109.4
O2—C1—C6120.02 (8)C8—C9—H9B109.4
C2—C1—C6122.90 (8)H9A—C9—H9B108.0
C3—C2—C1118.14 (8)C11—C10—C15118.14 (11)
C3—C2—H2A120.9C11—C10—C9121.36 (11)
C1—C2—H2A120.9C15—C10—C9120.50 (9)
O3—C3—C2123.84 (9)C10—C11—C12120.52 (15)
O3—C3—C4114.90 (9)C10—C11—H11A119.7
C2—C3—C4121.26 (7)C12—C11—H11A119.7
C5—C4—C3120.05 (8)C13—C12—C11120.27 (14)
C5—C4—H4A120.0C13—C12—H12A119.9
C3—C4—H4A120.0C11—C12—H12A119.9
O4—C5—C4120.48 (8)C14—C13—C12119.88 (13)
O4—C5—C6118.37 (7)C14—C13—H13A120.1
C4—C5—C6121.15 (8)C12—C13—H13A120.1
C5—C6—C1116.50 (7)C13—C14—C15119.88 (16)
C5—C6—C7124.74 (8)C13—C14—H14A120.1
C1—C6—C7118.76 (8)C15—C14—H14A120.1
O1—C7—C6120.09 (8)C10—C15—C14121.29 (13)
O1—C7—C8117.52 (7)C10—C15—H15A119.4
C6—C7—C8122.38 (8)C14—C15—H15A119.4
C7—C8—C9113.30 (7)O3—C16—H16A109.5
C7—C8—H8A108.9O3—C16—H16B109.5
C9—C8—H8A108.9H16A—C16—H16B109.5
C7—C8—H8B108.9O3—C16—H16C109.5
C9—C8—H8B108.9H16A—C16—H16C109.5
H8A—C8—H8B107.7H16B—C16—H16C109.5
O2—C1—C2—C3179.91 (8)C5—C6—C7—O1178.29 (8)
C6—C1—C2—C30.16 (14)C1—C6—C7—O11.64 (14)
C16—O3—C3—C21.66 (15)C5—C6—C7—C82.74 (15)
C16—O3—C3—C4178.47 (8)C1—C6—C7—C8177.33 (8)
C1—C2—C3—O3179.62 (8)O1—C7—C8—C93.30 (12)
C1—C2—C3—C40.24 (14)C6—C7—C8—C9175.70 (8)
O3—C3—C4—C5179.79 (8)C7—C8—C9—C10172.32 (8)
C2—C3—C4—C50.34 (14)C8—C9—C10—C11108.05 (11)
C3—C4—C5—O4179.38 (7)C8—C9—C10—C1572.21 (12)
C3—C4—C5—C61.01 (14)C15—C10—C11—C120.83 (17)
O4—C5—C6—C1179.33 (7)C9—C10—C11—C12178.92 (11)
C4—C5—C6—C11.05 (13)C10—C11—C12—C130.5 (2)
O4—C5—C6—C70.60 (14)C11—C12—C13—C140.4 (2)
C4—C5—C6—C7179.02 (8)C12—C13—C14—C151.0 (2)
O2—C1—C6—C5179.46 (8)C11—C10—C15—C140.27 (17)
C2—C1—C6—C50.46 (14)C9—C10—C15—C14179.47 (11)
O2—C1—C6—C70.47 (13)C13—C14—C15—C100.6 (2)
C2—C1—C6—C7179.60 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O10.821.712.4576 (11)150
O4—H1O4···O2i0.80 (3)1.90 (3)2.6920 (10)175 (3)
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC16H16O4
Mr272.29
Crystal system, space groupMonoclinic, Cc
Temperature (K)100
a, b, c (Å)7.2142 (6), 30.522 (2), 6.5587 (5)
β (°) 107.267 (2)
V3)1379.09 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.46 × 0.34 × 0.18
Data collection
DiffractometerBruker APEX DUO CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.958, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
17744, 3044, 2940
Rint0.025
(sin θ/λ)max1)0.807
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.097, 1.08
No. of reflections3044
No. of parameters186
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.34, 0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O10.821.712.4576 (11)150
O4—H1O4···O2i0.80 (3)1.90 (3)2.6920 (10)175 (3)
Symmetry code: (i) x+1, y, z+1/2.
 

Footnotes

1This paper is dedicated to Her Royal Highness Princess Maha Chakri Sirindhorn of Thailand on the occasion of her 55th Birthday Anniversary which fell on April 2nd, 2010.

Thomson Reuters ResearcherID: A-5085-2009.

§Additional correspondence author, e-mail: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

JJ and TK thank the Center of Excellence for Innovation in Chemistry (PERCH-CIC) and the Faculty of Science and Technology, Suratthani Rajabhat University, for financial support. The Natural Products Research Laboratory, School of Science, Mae Fah Luang University, is gratefully acknowledged for laboratory facilities. SC thanks the Prince of Songkla University for financial support. Mr Nawong Boonnak is acknowledged for providing useful information. The authors also thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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