(E)-1-(2-Fur­yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

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

doi:10.1107/S160053681004451X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3070-o3071

https://doi.org/10.1107/S160053681004451X

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(E)-1-(2-Furyl)-3-(3,4,5-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 28 October 2010; accepted 31 October 2010; online 6 November 2010)

The title molecule, C₁₆H₁₆O₅, is twisted; the dihedral angle between the furan and 3,4,5-trimethoxyphenyl rings is 12.14 (13)°. The two methoxy groups at the meta positions of the benzene ring are close to being coplanar with the ring [C—O—C—C = −0.6 (3) and 1.4 (3)°], whereas the third methoxy group, at the para position, is (+)-anticlinal with respect to the benzene ring [C—O—C—C = 104.9 (2)°]. In the crystal, molecules are linked by weak C—H⋯O bonds to stack along the b axis and further C—H⋯O interactions consolidate the structure.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Fun et al. (2010 ); Suwunwong et al. (2009 ). For background to and applications of chalcones, see: Batovska et al. (2007 ); Gu et al. (2009 ); Jung et al. (2008 ); Prasad et al. (2008 ); Saxena et al. (2007 ); Tewtrakul et al. (2003 ).

Experimental

Crystal data

C₁₆H₁₆O₅
M_r = 288.29
Orthorhombic, P n a 2₁
a = 24.2677 (4) Å
b = 3.9916 (1) Å
c = 14.0816 (2) Å
V = 1364.04 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.35 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.965, T_max = 0.978
17261 measured reflections
2063 independent reflections
1907 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.092
S = 1.06
2063 reflections
254 parameters
1 restraint
All H-atom parameters refined
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O1ⁱ	0.99 (3)	2.54 (3)	3.503 (3)	166 (2)
C15—H15B⋯O4ⁱⁱ	1.01 (3)	2.36 (3)	3.337 (3)	162 (2)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z.

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: https://doi.org/10.1107/S160053681004451X/hb5713sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004451X/hb5713Isup2.hkl

checkCIF report

Comment top

Chalcones are known to exhibit bioactivity including antimicrobial (Prasad et al., 2008), antifungal (Batovska et al., 2007), anticancer (Saxena et al., 2007) and HIV-1 protease inhibitory (Tewtrakul et al., 2003), as well as Non Linear Optical (NLO) (Gu et al., 2009) and fluorescence properties (Jung et al., 2008). In our on-going research on antibacterial activities, NLO and fluorescence properties of aryl/heteroaryl chalcones, we previously reported the crystal structures of (E)-1-(2-furyl)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-one (I) (Fun et al., 2010) and (E)-1-(2-thienyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (II) (Suwunwong et al., 2009). The title compound (III) was synthesized and its crystal structure was determined in order to gain structural details to explain the affects of the substituent groups and their positions on the fluorescence properties and how their crystal packing would affect the NLO properties of the compounds. Compound (I) crystallized out in the centrosymmetric C2/c space group which prohibits second order NLO properties whereas compounds (II) and (III) crystallized in non-centrosymmetric Pna2₁ space group and should possess the second order NLO properties.

The molecule of the title heteroaryl chalcone (Fig. 1) exists in an E configuration with respect to the C6═C7 double bond [1.340 (3) Å] with torsion angle C5–C6–C7–C8 = 174.83 (19)°. The molecule is twisted with the dihedral angle between the furan and 3,4,5-trimethoxyphenyl rings being 12.14 (13)°. The propenone unit (C5—C7/O1) is slightly deviated with the torsion angle O1–C5–C6–C7 = 8.0 (3)°. The three methoxy groups of the 3,4,5-trimethoxyphenyl unit have two different orientations: the two methoxy groups at the meta positions (at atom C10 and C12 positions) are co-planar with the attached benzene ring with torsion angles C14–O3–C10–C9 = -0.6 (3)° and C16–O5–C12–C13 = 1.4 (3)° whereas the third one at para position (at atom C11) is (+)-anti-clinally attached with the torsion angle C15–O4–C11—C10 = 104.9 (2)°. Otherwise, the bond distances in (III) are of normal values (Allen et al., 1987) and are comparable with the closely related structures (Fun et al., 2010; Suwunwong et al., 2009).

In the crystal (Fig. 2), the molecules are stacked into columns along the b axis and molecules within the stacks are linked by weak C15—H15B···O4 (Table 1) interactions.

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: Fun et al. (2010); Suwunwong et al. (2009). For background and applications to chalcones, see: Batovska et al. (2007); Gu et al. (2009); Jung et al. (2008); Prasad et al. (2008); Saxena et al. (2007); Tewtrakul et al. (2003).

Experimental top

The title compound was synthesized by the condensation of 3,4,5-trimethoxybenzaldehyde (0.39 g, 2 mmol) in ethanol (15 ml) with 2-furyl methylketone (0.22 g, 2 mmol) in ethanol (15 ml) in the presence of 20% NaOH(aq) (5 ml). After stirring for 4 h, the resulting pale yellow solid appeared and was then collected by filtration, washed with distilled water and dried (69% yield). Pale yellow blocks of (III) were recrystalized from acetone/methanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after several days, Mp. 420–421 K.

Structure description top

In the crystal (Fig. 2), the molecules are stacked into columns along the b axis and molecules within the stacks are linked by weak C15—H15B···O4 (Table 1) interactions.

For bond-length data, see: Allen et al. (1987). For hydrogen bond motifs, see: Bernstein et al. (1995). For related structures, see: Fun et al. (2010); Suwunwong et al. (2009). For background and applications to chalcones, see: Batovska et al. (2007); Gu et al. (2009); Jung et al. (2008); Prasad et al. (2008); Saxena et al. (2007); Tewtrakul et al. (2003).

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 (III), showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (III), showing column along the b axis. C—H···O weak interactions are shown as dashed lines.

(E)-1-(2-Furyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₆O₅	D_x = 1.404 Mg m⁻³
M_r = 288.29	Melting point = 420–421 K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2063 reflections
a = 24.2677 (4) Å	θ = 2.2–30.0°
b = 3.9916 (1) Å	µ = 0.11 mm⁻¹
c = 14.0816 (2) Å	T = 100 K
V = 1364.04 (5) Å³	Block, pale yellow
Z = 4	0.35 × 0.24 × 0.21 mm
F(000) = 608

Data collection top

Bruker APEXII CCD diffractometer	2063 independent reflections
Radiation source: sealed tube	1907 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 30.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −29→34
T_min = 0.965, T_max = 0.978	k = −5→5
17261 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0501P)² + 0.4265P] where P = (F_o² + 2F_c²)/3
2063 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.36 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₆O₅	V = 1364.04 (5) Å³
M_r = 288.29	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 24.2677 (4) Å	µ = 0.11 mm⁻¹
b = 3.9916 (1) Å	T = 100 K
c = 14.0816 (2) Å	0.35 × 0.24 × 0.21 mm

Data collection top

Bruker APEXII CCD diffractometer	2063 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1907 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.978	R_int = 0.035
17261 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.092	All H-atom parameters refined
S = 1.06	Δρ_max = 0.36 e Å⁻³
2063 reflections	Δρ_min = −0.22 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 e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.25005 (6)	0.6063 (4)	0.72174 (11)	0.0251 (3)
O2	0.34121 (7)	0.1635 (4)	0.87377 (12)	0.0271 (4)
O3	0.41052 (6)	0.5004 (4)	0.26993 (10)	0.0181 (3)
O4	0.50168 (6)	0.1761 (4)	0.32189 (11)	0.0181 (3)
O5	0.51882 (6)	−0.0146 (4)	0.50322 (11)	0.0190 (3)
C1	0.33965 (11)	0.1379 (8)	0.96954 (19)	0.0333 (6)
H1A	0.3722 (14)	0.001 (7)	0.995 (2)	0.036 (8)*
C2	0.29645 (12)	0.3011 (8)	1.00503 (17)	0.0342 (6)
H2A	0.2846 (17)	0.331 (11)	1.057 (3)	0.064 (13)*
C3	0.26677 (10)	0.4471 (7)	0.92549 (17)	0.0247 (5)
H3A	0.2426 (12)	0.568 (8)	0.922 (2)	0.026 (8)*
C4	0.29621 (8)	0.3538 (5)	0.84793 (14)	0.0171 (4)
C5	0.28952 (8)	0.4380 (5)	0.74728 (14)	0.0168 (4)
C6	0.33353 (8)	0.3224 (5)	0.68267 (15)	0.0171 (4)
H6A	0.3628 (11)	0.190 (7)	0.709 (2)	0.020 (6)*
C7	0.33640 (8)	0.4294 (5)	0.59260 (14)	0.0167 (4)
H7A	0.3082 (12)	0.566 (7)	0.570 (2)	0.023 (7)*
C8	0.37985 (8)	0.3565 (5)	0.52384 (13)	0.0155 (4)
C9	0.37237 (8)	0.4630 (5)	0.43008 (15)	0.0154 (3)
H9A	0.3401 (11)	0.568 (7)	0.410 (2)	0.019 (6)*
C10	0.41374 (8)	0.4064 (5)	0.36290 (13)	0.0143 (3)
C11	0.46246 (8)	0.2434 (5)	0.38936 (13)	0.0145 (3)
C12	0.46971 (8)	0.1383 (5)	0.48394 (14)	0.0151 (4)
C13	0.42857 (8)	0.1923 (5)	0.55057 (14)	0.0155 (4)
H13A	0.4332 (10)	0.125 (6)	0.615 (2)	0.014 (6)*
C14	0.36071 (8)	0.6651 (6)	0.24098 (15)	0.0189 (4)
H14C	0.3554 (11)	0.873 (7)	0.274 (2)	0.020 (7)*
H14B	0.3290 (12)	0.513 (7)	0.248 (2)	0.019 (7)*
H14A	0.3628 (12)	0.717 (7)	0.177 (2)	0.023 (7)*
C15	0.54913 (9)	0.3915 (6)	0.32550 (18)	0.0224 (4)
H15A	0.5639 (17)	0.395 (12)	0.393 (3)	0.069 (13)*
H15B	0.5367 (14)	0.627 (8)	0.309 (2)	0.040 (9)*
H15C	0.5741 (12)	0.315 (8)	0.277 (2)	0.032 (8)*
C16	0.52677 (9)	−0.1308 (6)	0.59880 (14)	0.0198 (4)
H16A	0.4975 (11)	−0.287 (7)	0.617 (2)	0.022 (7)*
H16B	0.5618 (12)	−0.249 (7)	0.598 (2)	0.023 (7)*
H16C	0.5293 (11)	0.058 (8)	0.645 (2)	0.021 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0218 (7)	0.0366 (8)	0.0169 (7)	0.0091 (7)	0.0035 (6)	0.0052 (7)
O2	0.0229 (7)	0.0313 (9)	0.0272 (9)	−0.0017 (7)	−0.0050 (6)	0.0068 (7)
O3	0.0184 (7)	0.0243 (7)	0.0114 (6)	0.0016 (6)	0.0005 (5)	0.0028 (5)
O4	0.0166 (6)	0.0244 (7)	0.0133 (6)	−0.0004 (6)	0.0038 (5)	−0.0033 (6)
O5	0.0166 (6)	0.0255 (7)	0.0149 (7)	0.0045 (6)	0.0004 (5)	0.0027 (6)
C1	0.0318 (12)	0.0426 (15)	0.0256 (12)	−0.0123 (11)	−0.0095 (9)	0.0101 (10)
C2	0.0455 (15)	0.0456 (15)	0.0113 (9)	−0.0270 (12)	0.0002 (10)	−0.0011 (10)
C3	0.0218 (9)	0.0340 (12)	0.0182 (10)	−0.0103 (10)	0.0068 (8)	−0.0077 (9)
C4	0.0156 (8)	0.0214 (9)	0.0142 (9)	−0.0018 (7)	0.0018 (7)	0.0023 (7)
C5	0.0161 (8)	0.0217 (9)	0.0126 (8)	−0.0029 (7)	0.0028 (7)	0.0009 (7)
C6	0.0154 (8)	0.0185 (9)	0.0175 (9)	0.0017 (7)	0.0017 (7)	−0.0001 (8)
C7	0.0126 (8)	0.0226 (10)	0.0149 (8)	0.0008 (7)	0.0017 (7)	−0.0017 (7)
C8	0.0142 (8)	0.0190 (9)	0.0134 (8)	−0.0022 (7)	0.0008 (6)	−0.0009 (7)
C9	0.0145 (7)	0.0187 (9)	0.0130 (8)	−0.0004 (7)	0.0001 (7)	−0.0006 (7)
C10	0.0162 (8)	0.0154 (8)	0.0112 (8)	−0.0023 (7)	−0.0006 (7)	−0.0001 (7)
C11	0.0141 (7)	0.0167 (8)	0.0127 (8)	−0.0017 (7)	0.0035 (6)	−0.0018 (7)
C12	0.0139 (8)	0.0160 (9)	0.0153 (9)	0.0003 (7)	−0.0017 (6)	−0.0016 (7)
C13	0.0164 (8)	0.0195 (9)	0.0107 (8)	−0.0022 (7)	0.0008 (7)	0.0002 (7)
C14	0.0185 (9)	0.0226 (10)	0.0157 (9)	0.0005 (8)	−0.0033 (7)	0.0026 (8)
C15	0.0196 (9)	0.0214 (10)	0.0262 (10)	−0.0027 (8)	0.0090 (8)	−0.0005 (9)
C16	0.0193 (9)	0.0240 (10)	0.0161 (9)	0.0014 (8)	−0.0025 (8)	0.0046 (8)

Geometric parameters (Å, º) top

O1—C5	1.224 (3)	C7—C8	1.461 (3)
O2—C1	1.353 (3)	C7—H7A	0.93 (3)
O2—C4	1.379 (3)	C8—C9	1.399 (3)
O3—C10	1.364 (2)	C8—C13	1.403 (3)
O3—C14	1.435 (2)	C9—C10	1.398 (3)
O4—C11	1.372 (2)	C9—H9A	0.93 (3)
O4—C15	1.438 (3)	C10—C11	1.400 (3)
O5—C12	1.366 (2)	C11—C12	1.407 (3)
O5—C16	1.437 (2)	C12—C13	1.387 (3)
C1—C2	1.332 (5)	C13—H13A	0.96 (3)
C1—H1A	1.03 (3)	C14—H14C	0.96 (3)
C2—C3	1.454 (4)	C14—H14B	0.99 (3)
C2—H2A	0.80 (5)	C14—H14A	0.93 (3)
C3—C4	1.357 (3)	C15—H15A	1.02 (5)
C3—H3A	0.76 (3)	C15—H15B	1.01 (3)
C4—C5	1.466 (3)	C15—H15C	0.96 (3)
C5—C6	1.477 (3)	C16—H16A	0.98 (3)
C6—C7	1.340 (3)	C16—H16B	0.97 (3)
C6—H6A	0.96 (3)	C16—H16C	1.00 (3)

C1—O2—C4	106.4 (2)	O3—C10—C9	124.33 (18)
C10—O3—C14	116.54 (16)	O3—C10—C11	115.57 (17)
C11—O4—C15	114.47 (16)	C9—C10—C11	120.10 (17)
C12—O5—C16	116.60 (16)	O4—C11—C10	119.52 (17)
C2—C1—O2	111.0 (2)	O4—C11—C12	120.68 (17)
C2—C1—H1A	137.1 (19)	C10—C11—C12	119.74 (17)
O2—C1—H1A	111.8 (19)	O5—C12—C13	124.26 (18)
C1—C2—C3	107.3 (2)	O5—C12—C11	115.50 (17)
C1—C2—H2A	135 (3)	C13—C12—C11	120.25 (17)
C3—C2—H2A	118 (3)	C12—C13—C8	119.85 (18)
C4—C3—C2	104.4 (2)	C12—C13—H13A	121.0 (15)
C4—C3—H3A	122 (3)	C8—C13—H13A	119.1 (15)
C2—C3—H3A	133 (3)	O3—C14—H14C	111.7 (17)
C3—C4—O2	110.8 (2)	O3—C14—H14B	110.3 (16)
C3—C4—C5	131.1 (2)	H14C—C14—H14B	112 (2)
O2—C4—C5	117.99 (17)	O3—C14—H14A	109.5 (18)
O1—C5—C4	119.79 (18)	H14C—C14—H14A	107 (3)
O1—C5—C6	123.80 (19)	H14B—C14—H14A	106 (2)
C4—C5—C6	116.36 (18)	O4—C15—H15A	109 (3)
C7—C6—C5	121.40 (19)	O4—C15—H15B	107.9 (19)
C7—C6—H6A	120.0 (17)	H15A—C15—H15B	108 (3)
C5—C6—H6A	118.1 (17)	O4—C15—H15C	106.8 (19)
C6—C7—C8	126.96 (19)	H15A—C15—H15C	116 (3)
C6—C7—H7A	118.4 (18)	H15B—C15—H15C	109 (3)
C8—C7—H7A	114.6 (18)	O5—C16—H16A	110.7 (17)
C9—C8—C13	120.28 (17)	O5—C16—H16B	105.3 (17)
C9—C8—C7	118.13 (18)	H16A—C16—H16B	109 (2)
C13—C8—C7	121.57 (17)	O5—C16—H16C	111.9 (18)
C10—C9—C8	119.77 (17)	H16A—C16—H16C	111 (2)
C10—C9—H9A	118.2 (18)	H16B—C16—H16C	109 (2)
C8—C9—H9A	122.0 (18)

C4—O2—C1—C2	−0.1 (3)	C14—O3—C10—C11	179.43 (17)
O2—C1—C2—C3	0.1 (3)	C8—C9—C10—O3	−179.95 (18)
C1—C2—C3—C4	−0.1 (3)	C8—C9—C10—C11	0.1 (3)
C2—C3—C4—O2	0.0 (2)	C15—O4—C11—C10	104.9 (2)
C2—C3—C4—C5	−175.9 (2)	C15—O4—C11—C12	−77.7 (2)
C1—O2—C4—C3	0.1 (3)	O3—C10—C11—O4	−2.9 (3)
C1—O2—C4—C5	176.5 (2)	C9—C10—C11—O4	177.11 (18)
C3—C4—C5—O1	−4.4 (4)	O3—C10—C11—C12	179.71 (18)
O2—C4—C5—O1	179.97 (19)	C9—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	172.9 (2)	C16—O5—C12—C13	1.4 (3)
O2—C4—C5—C6	−2.7 (3)	C16—O5—C12—C11	−178.70 (17)
O1—C5—C6—C7	8.0 (3)	O4—C11—C12—O5	3.4 (3)
C4—C5—C6—C7	−169.2 (2)	C10—C11—C12—O5	−179.21 (17)
C5—C6—C7—C8	174.83 (19)	O4—C11—C12—C13	−176.68 (18)
C6—C7—C8—C9	173.3 (2)	C10—C11—C12—C13	0.7 (3)
C6—C7—C8—C13	−8.3 (3)	O5—C12—C13—C8	179.05 (18)
C13—C8—C9—C10	−0.2 (3)	C11—C12—C13—C8	−0.8 (3)
C7—C8—C9—C10	178.14 (18)	C9—C8—C13—C12	0.6 (3)
C14—O3—C10—C9	−0.6 (3)	C7—C8—C13—C12	−177.69 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O1ⁱ	0.99 (3)	2.54 (3)	3.503 (3)	166 (2)
C15—H15B···O4ⁱⁱ	1.01 (3)	2.36 (3)	3.337 (3)	162 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆O₅
M_r	288.29
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	24.2677 (4), 3.9916 (1), 14.0816 (2)
V (Å³)	1364.04 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.35 × 0.24 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.965, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	17261, 2063, 1907
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.092, 1.06
No. of reflections	2063
No. of parameters	254
No. of restraints	1
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.22

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
C14—H14B···O1ⁱ	0.99 (3)	2.54 (3)	3.503 (3)	166 (2)
C15—H15B···O4ⁱⁱ	1.01 (3)	2.36 (3)	3.337 (3)	162 (2)

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

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 the research grant (RSA5280033) and the Prince of Songkla University for financial support. The authors also thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

References

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