(E)-1-(2-Fur­yl)-3-(2,4,6-trimeth­oxy­phen­yl)prop-2-en-1-one

Fun, H.-K.; Suwunwong, T.; Chantrapromma, S.; Karalai, C.

doi:10.1107/S1600536810035762

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2559-o2560

doi:10.1107/S1600536810035762

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(E)-1-(2-Furyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Thitipone Suwunwong,^b Suchada Chantrapromma ^b § and Chatchanok Karalai ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 31 August 2010; accepted 6 September 2010; online 15 September 2010)

In the title heteroaryl chalcone derivative, C₁₆H₁₆O₅, the dihedral angle between the furan and benzene rings is 14.45 (6)°. The three methoxy groups are almost coplanar with their attached benzene ring [C—C—O—C torsion angles = 2.07 (17), −5.04 (17) and 2.85 (16)°]. An intramolecular C—H⋯O hydrogen bond occurs. In the crystal, adjacent molecules are linked into X-shaped chains along the c axis by weak C—H⋯O(enone) interactions. These chains are stacked along the b axis. C⋯O [3.3308 (13)–3.4123 (14) Å] short contacts are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Chantrapromma et al. (2009 ); Suwunwong et al. (2009 . For background to and applications of chalcones and heteroaryl chalcones, see: Gaber et al. (2008 ); Go et al. (2005 ); Jung et al. (2008 ); Ng et al. (2009 ); Ni et al. (2004 ); Nowakowska (2007 ); Patil & Dharmaprakash (2008 ) and Tewtrakul et al. (2003 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ).

Experimental

Crystal data

C₁₆H₁₆O₅
M_r = 288.29
Monoclinic, C 2/c
a = 38.5688 (5) Å
b = 3.93493 (5) Å
c = 18.2638 (3) Å
β = 103.901 (1)°
V = 2690.68 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.41 × 0.15 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.957, T_max = 0.990
20657 measured reflections
3941 independent reflections
3077 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.113
S = 1.06
3941 reflections
254 parameters
All H-atom parameters refined
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	0.956 (15)	2.496 (15)	3.3512 (14)	148.9 (13)
C6—H6⋯O5	0.965 (15)	2.260 (14)	2.8197 (15)	116.0 (11)
C14—H14A⋯O4ⁱⁱ	0.975 (15)	2.589 (16)	3.4462 (14)	146.7 (11)
C15—H15A⋯O1ⁱⁱⁱ	0.989 (16)	2.546 (16)	3.4293 (18)	148.6 (12)
C16—H16A⋯O1ⁱⁱⁱ	0.982 (16)	2.575 (16)	3.4120 (16)	143.0 (12)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (ii) -x, -y, -z+1; (iii) $[x, -y, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035762/hb5630sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035762/hb5630Isup2.hkl

checkCIF report

Comment top

Chalcone and heteroaryl chalcones are very interesting due to their variety of applications with biological activities. Many of them possess analgesic, anti-inflammatory and antibacterial properties (Go et al., 2005; Ni et al., 2004; Nowakowska, 2007) as well as HIV-1 protease inhibitory (Tewtrakul et al., 2003) and tyrosinase inhibitory (Ng et al., 2009) activities. Moreover synthetic chalcones and heteroaryl chalcones have also been found to exhibit non-linear optical (Patil & Dharmaprakash, 2008), fluorescent (Jung et al., 2008) and laser properties (Gaber et al., 2008) . In continuing our on-going research on antibacterial activities and fluorescence properties of chalcones and heteroaryl chalcone derivatives, the title heteroaryl chalcone was synthesized in order to study its antibacterial and fluorescence properties. However our results show that (I) do not possess fluorescence property. In addition our biological testing found that (I) was inactive against the tested bacteria strains which are Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Methicillin-Resistant Staphylococcus aureus, Vancomycin-Resistant Enterococcus faecalis, Pseudomonas aeruginosa, Salmonella typhi and Shigella sonnei. Herein we report the crystal structure of (I).

The molecule of the title heteroaryl chalcone (Fig. 1) exists in an E configuration with respect to the C6═C7 double bond [1.3512 (16) Å] with the C5–C6–C7–C8 torsion angle being -176.44 (12)°. The whole molecule is slightly twisted with the dihedral angle between the furan and benzene rings being 14.45 (6)°. Atoms of the propenone unit (C5, C6, C7 and O1) lie on the same plane [r.m.s. 0.0179 (1)]. This plane makes dihedral angles of 11.38 (8) and 9.12 (8)° with furan and phenyl rings, respectively. All the three substituted methoxy groups of 2,4,6-trimethoxyphenyl unit are almost co-planar with the phenyl ring as indicated by torsion angles C14–O3–C9–C10 = 2.07 (17)°, C15–O4–C11–C12 = -5.04 (17)° and C16–O5–C13–C12 = 2.85 (16)°. In the structure, a weak intramolecular C6—H6···O5 interaction generates an S(6) ring motif (Bernstein et al., 1995) (Table 1). The bond lengths have normal values (Allen et al., 1987) and bond lengths and angles are comparable with its related structures (Chantrapromma et al., 2009; Suwunwong et al., 2009).

In the crystal packing, all the three methoxy groups involve in weak intermolecular C—H···O interactions (Table 1). The adjacent molecules are linked into X-shape chains along the c axis through the enone unit by weak C—H···O interactions (Fig. 2, Table 1). The adjacent chains are arranged into face-to-face manner (Fig. 3) and stacked along the b axis (Fig. 3). The crystal is further stabilized by C···O[3.3308 (13)-3.4123 (14) Å] short contacts.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Chantrapromma et al. (2009); Suwunwong et al. (2009. For background to and applications of chalcones and heteroaryl chalcones, see: Gaber et al. (2008); Go et al. (2005); Jung et al. (2008); Ng et al. (2009); Ni et al. (2004); Nowakowska (2007); Patil & Dharmaprakash (2008) and Tewtrakul et al. (2003). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental top

The title compound was prepared by the condensation of the solution of 2-furyl methylketone (2 mmol, 0.22 g) in ethanol (15 ml) and 2,4,6-trimethoxybenzaldehyde (2 mmol, 0.40 g) in ethanol (15 ml) in the presence of 20% NaOH (aq) 5 ml at 278 K for 5 hr. The resulting solid which was obtained was further collected by filtration, washed with distilled water and dried in air. Colorless blocks of (I) were recrystalized from acetone/ethanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after several days, Mp. 390–391 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. Weak intramolecular interactions are shown as dashed lines.
	Fig. 2. The crystal packing of (I) viewed along the c axis, showing X-chains running along the c axis. Weak C—H···O interactions are shown as dashed lines.
	Fig. 3. The crystal packing of (I) viewed along the b axis, showing chains stacking along the b axis. Weak C—H···O interactions are shown as dashed lines.

(E)-1-(2-Furyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₆O₅	F(000) = 1216
M_r = 288.29	D_x = 1.423 Mg m⁻³
Monoclinic, C2/c	Melting point = 390–391 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 38.5688 (5) Å	Cell parameters from 3941 reflections
b = 3.93493 (5) Å	θ = 1.1–30.0°
c = 18.2638 (3) Å	µ = 0.11 mm⁻¹
β = 103.901 (1)°	T = 100 K
V = 2690.68 (6) Å³	Block, colorless
Z = 8	0.41 × 0.15 × 0.09 mm

Data collection top

Bruker APEXII CCD diffractometer	3941 independent reflections
Radiation source: sealed tube	3077 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 30.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −54→54
T_min = 0.957, T_max = 0.990	k = −5→5
20657 measured reflections	l = −25→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0556P)² + 1.4768P] where P = (F_o² + 2F_c²)/3
3941 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₆O₅	V = 2690.68 (6) Å³
M_r = 288.29	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 38.5688 (5) Å	µ = 0.11 mm⁻¹
b = 3.93493 (5) Å	T = 100 K
c = 18.2638 (3) Å	0.41 × 0.15 × 0.09 mm
β = 103.901 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3941 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3077 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.990	R_int = 0.038
20657 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.113	All H-atom parameters refined
S = 1.06	Δρ_max = 0.35 e Å⁻³
3941 reflections	Δρ_min = −0.24 e Å⁻³
254 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 120.0 (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

	x	y	z	U_iso*/U_eq
O1	0.15077 (2)	0.0988 (3)	0.84899 (5)	0.0215 (2)
O2	0.21727 (2)	0.3478 (2)	0.90839 (4)	0.01663 (19)
O3	0.05690 (2)	−0.2197 (2)	0.65467 (5)	0.01694 (19)
O4	0.04708 (2)	−0.1724 (2)	0.39117 (5)	0.01735 (19)
O5	0.15024 (2)	0.2851 (2)	0.56781 (5)	0.01639 (19)
C1	0.25039 (3)	0.4913 (3)	0.92049 (7)	0.0174 (2)
H1	0.2651 (4)	0.474 (4)	0.9706 (8)	0.018 (4)*
C2	0.25591 (3)	0.6274 (3)	0.85645 (7)	0.0188 (3)
H2	0.2775 (4)	0.741 (4)	0.8513 (9)	0.027 (4)*
C3	0.22403 (3)	0.5659 (3)	0.79963 (7)	0.0174 (2)
H3	0.2194 (4)	0.630 (4)	0.7461 (9)	0.021 (4)*
C4	0.20144 (3)	0.3929 (3)	0.83315 (6)	0.0141 (2)
C5	0.16581 (3)	0.2391 (3)	0.80482 (6)	0.0150 (2)
C6	0.15171 (3)	0.2521 (3)	0.72275 (7)	0.0153 (2)
H6	0.1649 (4)	0.381 (4)	0.6935 (8)	0.019 (4)*
C7	0.12181 (3)	0.0762 (3)	0.69077 (6)	0.0145 (2)
H7	0.1101 (4)	−0.049 (4)	0.7240 (8)	0.020 (4)*
C8	0.10376 (3)	0.0332 (3)	0.61194 (6)	0.0133 (2)
C9	0.06997 (3)	−0.1318 (3)	0.59416 (6)	0.0132 (2)
C10	0.05156 (3)	−0.1931 (3)	0.52043 (7)	0.0150 (2)
H10	0.0282 (4)	−0.310 (4)	0.5082 (9)	0.027 (4)*
C11	0.06682 (3)	−0.0939 (3)	0.46185 (6)	0.0140 (2)
C12	0.09968 (3)	0.0689 (3)	0.47557 (6)	0.0139 (2)
H12	0.1100 (4)	0.127 (4)	0.4359 (8)	0.018 (4)*
C13	0.11766 (3)	0.1321 (3)	0.55034 (6)	0.0131 (2)
C14	0.02326 (3)	−0.3920 (3)	0.63942 (7)	0.0177 (2)
H14A	0.0040 (4)	−0.255 (4)	0.6091 (8)	0.018 (4)*
H14B	0.0253 (4)	−0.612 (4)	0.6129 (8)	0.021 (4)*
H14C	0.0183 (4)	−0.431 (4)	0.6887 (9)	0.023 (4)*
C15	0.06015 (4)	−0.0546 (4)	0.32866 (7)	0.0206 (3)
H15A	0.0833 (4)	−0.158 (4)	0.3269 (9)	0.024 (4)*
H15B	0.0411 (5)	−0.122 (4)	0.2834 (9)	0.032 (4)*
H15C	0.0620 (4)	0.196 (4)	0.3296 (9)	0.024 (4)*
C16	0.16511 (3)	0.3953 (3)	0.50694 (7)	0.0158 (2)
H16A	0.1703 (4)	0.200 (4)	0.4778 (9)	0.021 (4)*
H16B	0.1490 (4)	0.555 (4)	0.4762 (8)	0.015 (3)*
H16C	0.1875 (4)	0.511 (4)	0.5307 (8)	0.020 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0194 (4)	0.0314 (5)	0.0145 (4)	−0.0052 (4)	0.0057 (3)	0.0020 (4)
O2	0.0151 (4)	0.0227 (5)	0.0111 (4)	−0.0018 (3)	0.0012 (3)	0.0000 (3)
O3	0.0143 (4)	0.0231 (5)	0.0142 (4)	−0.0047 (3)	0.0049 (3)	0.0000 (3)
O4	0.0162 (4)	0.0239 (5)	0.0111 (4)	−0.0038 (3)	0.0015 (3)	−0.0018 (3)
O5	0.0130 (4)	0.0242 (5)	0.0119 (4)	−0.0051 (3)	0.0029 (3)	0.0009 (3)
C1	0.0152 (5)	0.0204 (6)	0.0157 (6)	−0.0013 (4)	0.0017 (4)	−0.0018 (5)
C2	0.0174 (6)	0.0211 (6)	0.0182 (6)	−0.0039 (5)	0.0049 (5)	−0.0022 (5)
C3	0.0193 (6)	0.0193 (6)	0.0133 (5)	−0.0018 (4)	0.0037 (4)	−0.0014 (5)
C4	0.0152 (5)	0.0171 (6)	0.0094 (5)	0.0016 (4)	0.0016 (4)	−0.0009 (4)
C5	0.0149 (5)	0.0171 (6)	0.0131 (5)	0.0011 (4)	0.0038 (4)	−0.0007 (4)
C6	0.0155 (5)	0.0172 (6)	0.0131 (5)	−0.0002 (4)	0.0033 (4)	0.0004 (4)
C7	0.0146 (5)	0.0169 (6)	0.0122 (5)	0.0018 (4)	0.0038 (4)	−0.0003 (4)
C8	0.0129 (5)	0.0147 (5)	0.0124 (5)	0.0009 (4)	0.0032 (4)	−0.0001 (4)
C9	0.0135 (5)	0.0139 (5)	0.0129 (5)	0.0006 (4)	0.0048 (4)	0.0008 (4)
C10	0.0125 (5)	0.0170 (6)	0.0150 (5)	−0.0007 (4)	0.0027 (4)	−0.0006 (4)
C11	0.0132 (5)	0.0153 (6)	0.0121 (5)	0.0011 (4)	0.0003 (4)	−0.0012 (4)
C12	0.0133 (5)	0.0163 (6)	0.0121 (5)	0.0014 (4)	0.0031 (4)	0.0006 (4)
C13	0.0106 (5)	0.0133 (5)	0.0152 (5)	−0.0001 (4)	0.0028 (4)	0.0002 (4)
C14	0.0142 (5)	0.0197 (6)	0.0199 (6)	−0.0029 (4)	0.0058 (5)	0.0018 (5)
C15	0.0232 (6)	0.0265 (7)	0.0117 (5)	−0.0043 (5)	0.0036 (5)	0.0000 (5)
C16	0.0143 (5)	0.0205 (6)	0.0133 (5)	−0.0023 (4)	0.0043 (4)	0.0024 (5)

Geometric parameters (Å, º) top

O1—C5	1.2315 (14)	C7—C8	1.4507 (16)
O2—C1	1.3652 (14)	C7—H7	0.974 (15)
O2—C4	1.3745 (13)	C8—C13	1.4123 (15)
O3—C9	1.3648 (13)	C8—C9	1.4220 (15)
O3—C14	1.4307 (14)	C9—C10	1.3844 (16)
O4—C11	1.3673 (14)	C10—C11	1.3949 (16)
O4—C15	1.4317 (15)	C10—H10	0.988 (16)
O5—C13	1.3602 (13)	C11—C12	1.3883 (16)
O5—C16	1.4352 (14)	C12—C13	1.3974 (16)
C1—C2	1.3492 (17)	C12—H12	0.936 (15)
C1—H1	0.956 (15)	C14—H14A	0.976 (15)
C2—C3	1.4264 (17)	C14—H14B	1.003 (16)
C2—H2	0.970 (16)	C14—H14C	0.977 (16)
C3—C4	1.3617 (17)	C15—H15A	0.989 (16)
C3—H3	0.984 (15)	C15—H15B	1.001 (17)
C4—C5	1.4766 (16)	C15—H15C	0.990 (17)
C5—C6	1.4675 (16)	C16—H16A	0.982 (16)
C6—C7	1.3512 (16)	C16—H16B	0.963 (15)
C6—H6	0.967 (15)	C16—H16C	0.982 (16)

C1—O2—C4	106.39 (9)	C9—C10—C11	119.01 (10)
C9—O3—C14	117.18 (9)	C9—C10—H10	121.8 (9)
C11—O4—C15	117.18 (9)	C11—C10—H10	119.2 (9)
C13—O5—C16	118.08 (9)	O4—C11—C12	123.50 (10)
C2—C1—O2	111.12 (10)	O4—C11—C10	114.76 (10)
C2—C1—H1	132.6 (9)	C12—C11—C10	121.74 (10)
O2—C1—H1	116.2 (9)	C11—C12—C13	118.39 (10)
C1—C2—C3	105.98 (11)	C11—C12—H12	120.9 (9)
C1—C2—H2	125.8 (10)	C13—C12—H12	120.7 (9)
C3—C2—H2	128.2 (10)	O5—C13—C12	121.43 (10)
C4—C3—C2	106.90 (11)	O5—C13—C8	116.18 (10)
C4—C3—H3	126.4 (9)	C12—C13—C8	122.37 (10)
C2—C3—H3	126.7 (9)	O3—C14—H14A	112.3 (9)
C3—C4—O2	109.60 (10)	O3—C14—H14B	109.3 (8)
C3—C4—C5	133.59 (11)	H14A—C14—H14B	109.8 (12)
O2—C4—C5	116.74 (10)	O3—C14—H14C	105.3 (9)
O1—C5—C6	124.57 (11)	H14A—C14—H14C	108.5 (12)
O1—C5—C4	119.95 (10)	H14B—C14—H14C	111.5 (13)
C6—C5—C4	115.40 (10)	O4—C15—H15A	112.7 (9)
C7—C6—C5	119.48 (11)	O4—C15—H15B	104.0 (10)
C7—C6—H6	122.6 (9)	H15A—C15—H15B	110.8 (13)
C5—C6—H6	117.9 (9)	O4—C15—H15C	110.3 (9)
C6—C7—C8	130.17 (11)	H15A—C15—H15C	110.6 (13)
C6—C7—H7	117.8 (9)	H15B—C15—H15C	108.2 (14)
C8—C7—H7	112.0 (9)	O5—C16—H16A	110.8 (9)
C13—C8—C9	116.51 (10)	O5—C16—H16B	109.1 (8)
C13—C8—C7	125.09 (10)	H16A—C16—H16B	112.5 (12)
C9—C8—C7	118.36 (10)	O5—C16—H16C	105.8 (8)
O3—C9—C10	122.72 (10)	H16A—C16—H16C	109.3 (12)
O3—C9—C8	115.31 (10)	H16B—C16—H16C	109.2 (13)
C10—C9—C8	121.96 (10)

C4—O2—C1—C2	0.63 (14)	C7—C8—C9—O3	3.17 (16)
O2—C1—C2—C3	−0.01 (15)	C13—C8—C9—C10	0.06 (17)
C1—C2—C3—C4	−0.63 (14)	C7—C8—C9—C10	−177.77 (11)
C2—C3—C4—O2	1.03 (14)	O3—C9—C10—C11	179.79 (11)
C2—C3—C4—C5	−175.73 (13)	C8—C9—C10—C11	0.80 (18)
C1—O2—C4—C3	−1.03 (13)	C15—O4—C11—C12	−5.04 (17)
C1—O2—C4—C5	176.35 (10)	C15—O4—C11—C10	175.53 (11)
C3—C4—C5—O1	−178.75 (13)	C9—C10—C11—O4	178.49 (10)
O2—C4—C5—O1	4.67 (17)	C9—C10—C11—C12	−0.95 (18)
C3—C4—C5—C6	4.4 (2)	O4—C11—C12—C13	−179.17 (11)
O2—C4—C5—C6	−172.18 (10)	C10—C11—C12—C13	0.22 (18)
O1—C5—C6—C7	−6.08 (19)	C16—O5—C13—C12	2.85 (16)
C4—C5—C6—C7	170.60 (11)	C16—O5—C13—C8	−178.91 (10)
C5—C6—C7—C8	−176.44 (12)	C11—C12—C13—O5	178.81 (10)
C6—C7—C8—C13	10.2 (2)	C11—C12—C13—C8	0.69 (18)
C6—C7—C8—C9	−172.18 (12)	C9—C8—C13—O5	−179.03 (10)
C14—O3—C9—C10	2.07 (17)	C7—C8—C13—O5	−1.37 (17)
C14—O3—C9—C8	−178.87 (10)	C9—C8—C13—C12	−0.82 (17)
C13—C8—C9—O3	−179.00 (10)	C7—C8—C13—C12	176.84 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.956 (15)	2.496 (15)	3.3512 (14)	148.9 (13)
C6—H6···O5	0.965 (15)	2.260 (14)	2.8197 (15)	116.0 (11)
C14—H14A···O4ⁱⁱ	0.975 (15)	2.589 (16)	3.4462 (14)	146.7 (11)
C15—H15A···O1ⁱⁱⁱ	0.989 (16)	2.546 (16)	3.4293 (18)	148.6 (12)
C16—H16A···O1ⁱⁱⁱ	0.982 (16)	2.575 (16)	3.4120 (16)	143.0 (12)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) −x, −y, −z+1; (iii) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆O₅
M_r	288.29
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	38.5688 (5), 3.93493 (5), 18.2638 (3)
β (°)	103.901 (1)
V (Å³)	2690.68 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.41 × 0.15 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.957, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	20657, 3941, 3077
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.113, 1.06
No. of reflections	3941
No. of parameters	254
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.956 (15)	2.496 (15)	3.3512 (14)	148.9 (13)
C6—H6···O5	0.965 (15)	2.260 (14)	2.8197 (15)	116.0 (11)
C14—H14A···O4ⁱⁱ	0.975 (15)	2.589 (16)	3.4462 (14)	146.7 (11)
C15—H15A···O1ⁱⁱⁱ	0.989 (16)	2.546 (16)	3.4293 (18)	148.6 (12)
C16—H16A···O1ⁱⁱⁱ	0.982 (16)	2.575 (16)	3.4120 (16)	143.0 (12)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+2; (ii) −x, −y, −z+1; (iii) x, −y, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

The authors thank the Thailand Research Fund (TRF) for a research grant (RSA 5280033) and the Prince of Songkla University for financial support. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811160. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is acknowledged for the bacterial assay.

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