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

Fun, H.-K.; Suwunwong, T.; Chanawanno, K.; Wisitsak, P.; Chantrapromma, S.

doi:10.1107/S1600536811031382

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2287-o2288

doi:10.1107/S1600536811031382

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

Hoong-Kun Fun,^a ^*‡ Thitipone Suwunwong,^b Kullapa Chanawanno,^b Pitikan Wisitsak ^c and Suchada Chantrapromma ^b §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cExcellence Center, Mae Fah Luang University, Thasud, Muang, Chaing Rai 57100, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 26 July 2011; accepted 3 August 2011; online 11 August 2011)

In the title chalcone derivative, C₁₈H₁₈O₅, the dihedral angle between the hydroxy-substituted benzene ring and the trimethoxy-substituted benzene ring is 16.3 (1)°. The three methoxy groups are essentially coplanar with the benzene ring to which they are attached, with an r.m.s. deviation of 0.0208 Å. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, weak C—H⋯O interactions link molecules into helical chains along the b axis. These chains are connected into sheets parallel to the bc plane by further weak C—H⋯O interactions.

Related literature

For background to and applications of chalcones, see: Boeck et al. (2006 ); Cheng et al. (2008 ); Hatayama et al. (2010 ); Jung et al. (2008 ); Lee et al. (2006 ); Liu et al. (2011 ); Nerya et al. (2004 ); Patil & Dharmaprakash (2008 ); Saydam et al. (2003 ); Tewtrakul et al. (2003 ). For related structures, see: Suwunwong et al. (2009 ); Fun et al. (2010 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For standard bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₈O₅
M_r = 314.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.2891 (2) Å
b = 17.3341 (9) Å
c = 20.5732 (10) Å
V = 1529.57 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.56 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.946, T_max = 0.986
16077 measured reflections
2392 independent reflections
1946 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.095
S = 1.08
2392 reflections
280 parameters
All H-atom parameters refined
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.89 (3)	1.73 (3)	2.541 (2)	152 (2)
C5—H5A⋯O5ⁱ	0.96 (2)	2.57 (2)	3.254 (3)	129.0 (18)
C16—H16C⋯O1ⁱⁱ	1.04 (3)	2.42 (3)	3.446 (3)	167.5 (18)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536811031382/lh5295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031382/lh5295Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031382/lh5295Isup3.cml

checkCIF report

Comment top

Chalcones or 1,3-diphenyl-2-propen-1-ones are commonly found in the natural products (Hatayama et al., 2010). They have a wide range of applications including non-linear optical effects (Patil & Dharmaprakash, 2008) in fluorescent materials (Jung et al., 2008) and have biological activities such as antibacterial (Liu et al., 2011), anti-inflammatory (Lee et al., 2006), antileishmanial (Boeck et al., 2006), cytotoxic (Saydam et al., 2003), anti-oxidant (Cheng et al., 2008), HIV-1 protease inhibitory (Tewtrakul et al., 2003) as well as anti-tyrosinase activities (Nerya et al., 2004). The various interesting applications of chalcones lead us to synthesize the title chalcone derivative in order to study its tyrosinase inhibitory activity and also to compare its properies with the previously published related compounds (Suwunwong et al., 2009; Fun et al., 2010). Our experiment shows that (I) exhibits tyrosinase inhibitory activity with the IC₅₀ value of 0.075 ± 0.000 mg ml^-1. Its tyrosinase inhibitory activity is therefore about 0.08 times that of the standard anti-tyrosinase kojic acid. Herein the crystal structure of (I) is reported.

The molecule of (I) in Fig. 1 exists in an E configuration with respect to the C8═C9 double bond [1.343 (3) Å]. The molecule is twisted with the dihedral angle between the 2-hydroxyphenyl and the 2,4,5-trimethoxyphenyl benzene rings being 16.3 (1)°. The middle prop-2-en-1-one unit (O2/C7–C9) is slightly twisted with the torsion angle O2–C7–C8–C9 = -8.8 (3)°. The mean plane through this unit makes dihedral angles of 13.48 (14)° and 2.85 (14)° with the 2-hydroxyphenyl and the 2,4,5-trimethoxyphenyl benzene rings, respectively. The three methoxy groups of 2,4,5-trimethoxyphenyl unit are essentially co-planar with the attached benzene ring with torsion angles C16–O3–C11–C12 = -1.0 (3)°, C17–O4–C13–C12 = -2.5 (3)° and C18–O5–C14–C15 = 3.1 (3)°. An O1—H1O1···O2 intramolecular hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995) (Table 1). The bond distances have of normal values (Allen et al., 1987) and are comparable with closely related structures (Suwunwong et al., 2009; Fun et al., 2010).

In the crystal packing (Fig. 2), weak C16—H16C···O1ⁱⁱ interactions (Table 1) link the molecules into helical chains along the b axis. These chains are further connected by weak C5—H5A···O5ⁱ interactions (Table 1) into supramolecular sheets parallel to the bc plane and stacked along the a axis.

Related literature top

For background to and applications of chalcones, see: Boeck et al. (2006); Cheng et al. (2008); Hatayama et al. (2010); Jung et al. (2008); Lee et al. (2006); Liu et al. (2011); Nerya et al. (2004); Patil & Dharmaprakash (2008); Saydam et al. (2003); Tewtrakul et al. (2003). For related structures, see: Suwunwong et al. (2009); Fun et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by stirring the mixed solution of 2-hydroxyacetophenone (0.24 ml, 2 mmol) and 2,4,5-trimethoxybenzaldehyde (0.40 g, 2 mmol) in ethanol (30 ml) in the presence of 10% NaOH(aq) (5 ml). After 4 h of stirring at room temperature, the orange solid was obtained and was then collected by filtration, washed with distilled water, dried and purified by recrystallization from hot acetone. Yellow block-shaped single crystals suitable for x-ray structure determination were grown over a period of several days by slow evaporation of the acetone/ethanol (1:1 v/v) solvent at room temperature, Mp. 404–405 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 the title compound, showing 50% probability displacement ellipsoids. An intramolecular O—H···O hydrogen bonds is shown as dashed line.
	Fig. 2. The crystal packing of the title compound, showing supramolecular sheets. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₈H₁₈O₅	D_x = 1.365 Mg m⁻³
M_r = 314.32	Melting point = 404–405 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2392 reflections
a = 4.2891 (2) Å	θ = 2.0–29.0°
b = 17.3341 (9) Å	µ = 0.10 mm⁻¹
c = 20.5732 (10) Å	T = 100 K
V = 1529.57 (13) Å³	Block, yellow
Z = 4	0.56 × 0.16 × 0.14 mm
F(000) = 664

Data collection top

Bruker APEXII CCD area-detector diffractometer	2392 independent reflections
Radiation source: sealed tube	1946 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 29.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
T_min = 0.946, T_max = 0.986	k = −23→17
16077 measured reflections	l = −24→27

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) = 0.095	All H-atom parameters refined
S = 1.08	w = 1/[σ²(F_o²) + (0.0466P)² + 0.2277P] where P = (F_o² + 2F_c²)/3
2392 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₈H₁₈O₅	V = 1529.57 (13) Å³
M_r = 314.32	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.2891 (2) Å	µ = 0.10 mm⁻¹
b = 17.3341 (9) Å	T = 100 K
c = 20.5732 (10) Å	0.56 × 0.16 × 0.14 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2392 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1946 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.986	R_int = 0.045
16077 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.095	All H-atom parameters refined
S = 1.08	Δρ_max = 0.25 e Å⁻³
2392 reflections	Δρ_min = −0.20 e Å⁻³
280 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	−0.2483 (4)	0.67956 (9)	0.11729 (7)	0.0294 (4)
O2	0.0456 (4)	0.56059 (8)	0.15537 (6)	0.0277 (4)
O3	0.5147 (4)	0.34185 (8)	0.25185 (6)	0.0239 (4)
O4	0.3357 (4)	0.08107 (8)	0.17331 (7)	0.0241 (4)
O5	−0.0186 (4)	0.13159 (7)	0.08358 (6)	0.0228 (4)
C1	−0.3401 (5)	0.63667 (11)	0.06566 (9)	0.0205 (5)
C2	−0.5266 (6)	0.67134 (12)	0.01880 (10)	0.0245 (5)
C3	−0.6134 (6)	0.63167 (13)	−0.03616 (11)	0.0267 (5)
C4	−0.5151 (6)	0.55587 (12)	−0.04557 (10)	0.0254 (5)
C5	−0.3396 (5)	0.52027 (12)	0.00162 (10)	0.0214 (5)
C6	−0.2498 (5)	0.55849 (11)	0.05878 (9)	0.0181 (4)
C7	−0.0708 (5)	0.52102 (11)	0.11099 (9)	0.0194 (4)
C8	−0.0393 (6)	0.43673 (11)	0.11163 (9)	0.0189 (4)
C9	0.1472 (5)	0.40085 (12)	0.15445 (10)	0.0197 (5)
C10	0.1985 (5)	0.31843 (11)	0.16063 (9)	0.0178 (4)
C11	0.3882 (5)	0.28887 (11)	0.21024 (9)	0.0188 (4)
C12	0.4385 (5)	0.20945 (12)	0.21658 (9)	0.0197 (5)
C13	0.3018 (5)	0.15894 (11)	0.17306 (9)	0.0183 (4)
C14	0.1069 (5)	0.18730 (11)	0.12307 (9)	0.0178 (4)
C15	0.0587 (5)	0.26522 (11)	0.11777 (9)	0.0174 (4)
C16	0.7030 (6)	0.31494 (14)	0.30485 (10)	0.0256 (5)
C17	0.5405 (6)	0.04847 (13)	0.22131 (12)	0.0267 (5)
C18	−0.2027 (6)	0.15760 (14)	0.03089 (11)	0.0236 (5)
H2A	−0.586 (6)	0.7230 (14)	0.0249 (10)	0.033 (7)*
H3A	−0.739 (7)	0.6549 (13)	−0.0687 (10)	0.029 (6)*
H4A	−0.557 (6)	0.5303 (12)	−0.0823 (10)	0.021 (6)*
H5A	−0.280 (6)	0.4677 (13)	−0.0057 (10)	0.029 (6)*
H8A	−0.163 (6)	0.4083 (11)	0.0806 (9)	0.015 (5)*
H9A	0.258 (6)	0.4335 (12)	0.1827 (9)	0.022 (6)*
H12A	0.568 (6)	0.1911 (12)	0.2488 (9)	0.019 (6)*
H15A	−0.079 (6)	0.2835 (12)	0.0829 (9)	0.020 (6)*
H16A	0.766 (7)	0.3640 (14)	0.3280 (10)	0.036 (7)*
H16B	0.890 (6)	0.2889 (13)	0.2889 (10)	0.028 (6)*
H16C	0.574 (7)	0.2787 (14)	0.3348 (10)	0.033 (6)*
H17A	0.467 (7)	0.0620 (13)	0.2662 (11)	0.040 (7)*
H17B	0.757 (7)	0.0676 (13)	0.2147 (11)	0.031 (7)*
H17C	0.539 (6)	−0.0083 (13)	0.2145 (9)	0.027 (6)*
H18A	−0.274 (6)	0.1128 (13)	0.0074 (9)	0.023 (6)*
H18B	−0.088 (6)	0.1914 (12)	0.0019 (10)	0.021 (6)*
H18C	−0.394 (7)	0.1848 (14)	0.0468 (10)	0.032 (7)*
H1O1	−0.123 (7)	0.6493 (15)	0.1401 (11)	0.042 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0418 (10)	0.0179 (8)	0.0286 (8)	0.0059 (8)	−0.0036 (9)	−0.0062 (7)
O2	0.0388 (10)	0.0186 (7)	0.0257 (7)	0.0033 (8)	−0.0077 (8)	−0.0047 (6)
O3	0.0308 (9)	0.0202 (7)	0.0207 (7)	−0.0013 (8)	−0.0069 (7)	−0.0022 (6)
O4	0.0311 (9)	0.0154 (7)	0.0256 (7)	0.0029 (7)	−0.0058 (7)	0.0032 (6)
O5	0.0307 (9)	0.0168 (7)	0.0208 (7)	0.0004 (7)	−0.0068 (7)	−0.0008 (5)
C1	0.0220 (11)	0.0172 (10)	0.0222 (10)	−0.0009 (9)	0.0066 (9)	0.0001 (8)
C2	0.0265 (12)	0.0155 (10)	0.0316 (11)	0.0015 (10)	0.0039 (10)	0.0023 (9)
C3	0.0269 (13)	0.0248 (12)	0.0283 (12)	0.0010 (10)	−0.0028 (11)	0.0085 (9)
C4	0.0311 (13)	0.0229 (11)	0.0221 (10)	−0.0027 (11)	−0.0029 (11)	0.0003 (9)
C5	0.0263 (12)	0.0151 (10)	0.0226 (10)	0.0002 (10)	0.0029 (10)	0.0003 (8)
C6	0.0188 (11)	0.0149 (10)	0.0206 (9)	−0.0012 (9)	0.0045 (9)	0.0019 (8)
C7	0.0211 (11)	0.0182 (10)	0.0189 (9)	−0.0001 (9)	0.0050 (9)	−0.0012 (8)
C8	0.0225 (11)	0.0167 (10)	0.0176 (9)	−0.0014 (9)	0.0023 (9)	−0.0011 (8)
C9	0.0223 (11)	0.0189 (10)	0.0178 (9)	−0.0022 (9)	0.0045 (9)	−0.0028 (8)
C10	0.0207 (10)	0.0181 (10)	0.0146 (9)	0.0022 (9)	0.0026 (9)	0.0001 (8)
C11	0.0204 (11)	0.0195 (10)	0.0164 (9)	−0.0009 (9)	0.0036 (9)	−0.0020 (8)
C12	0.0206 (11)	0.0228 (11)	0.0156 (9)	0.0023 (9)	−0.0003 (9)	0.0030 (8)
C13	0.0208 (11)	0.0153 (10)	0.0188 (9)	0.0013 (9)	0.0037 (9)	0.0034 (8)
C14	0.0205 (11)	0.0168 (10)	0.0162 (9)	−0.0006 (9)	0.0027 (9)	−0.0014 (8)
C15	0.0190 (10)	0.0193 (10)	0.0139 (9)	0.0015 (9)	0.0008 (9)	0.0021 (8)
C16	0.0287 (13)	0.0278 (13)	0.0202 (11)	−0.0017 (11)	−0.0052 (10)	0.0018 (9)
C17	0.0314 (14)	0.0196 (12)	0.0291 (12)	0.0059 (11)	−0.0038 (12)	0.0066 (9)
C18	0.0266 (13)	0.0217 (12)	0.0226 (11)	0.0003 (11)	−0.0066 (11)	−0.0003 (9)

Geometric parameters (Å, º) top

O1—C1	1.355 (2)	C8—C9	1.343 (3)
O1—H1O1	0.89 (3)	C8—H8A	0.96 (2)
O2—C7	1.246 (2)	C9—C10	1.451 (3)
O3—C11	1.368 (2)	C9—H9A	0.94 (2)
O3—C16	1.435 (3)	C10—C11	1.402 (3)
O4—C13	1.358 (2)	C10—C15	1.410 (3)
O4—C17	1.437 (3)	C11—C12	1.400 (3)
O5—C14	1.372 (2)	C12—C13	1.383 (3)
O5—C18	1.415 (3)	C12—H12A	0.92 (2)
C1—C2	1.389 (3)	C13—C14	1.413 (3)
C1—C6	1.417 (3)	C14—C15	1.371 (3)
C2—C3	1.375 (3)	C15—H15A	0.98 (2)
C2—H2A	0.94 (2)	C16—H16A	1.01 (2)
C3—C4	1.394 (3)	C16—H16B	0.98 (3)
C3—H3A	0.95 (2)	C16—H16C	1.04 (2)
C4—C5	1.375 (3)	C17—H17A	1.00 (2)
C4—H4A	0.89 (2)	C17—H17B	1.00 (3)
C5—C6	1.404 (3)	C17—H17C	0.99 (2)
C5—H5A	0.96 (2)	C18—H18A	0.96 (2)
C6—C7	1.471 (3)	C18—H18B	0.97 (2)
C7—C8	1.467 (3)	C18—H18C	1.00 (3)

C1—O1—H1O1	105.5 (16)	O3—C11—C12	122.76 (18)
C11—O3—C16	118.72 (16)	O3—C11—C10	116.12 (17)
C13—O4—C17	117.32 (16)	C12—C11—C10	121.11 (19)
C14—O5—C18	116.65 (16)	C13—C12—C11	119.82 (19)
O1—C1—C2	118.27 (18)	C13—C12—H12A	120.2 (13)
O1—C1—C6	121.59 (19)	C11—C12—H12A	119.9 (13)
C2—C1—C6	120.13 (19)	O4—C13—C12	125.57 (18)
C3—C2—C1	120.7 (2)	O4—C13—C14	114.32 (17)
C3—C2—H2A	120.9 (14)	C12—C13—C14	120.11 (17)
C1—C2—H2A	118.4 (14)	C15—C14—O5	125.95 (18)
C2—C3—C4	120.3 (2)	C15—C14—C13	119.32 (18)
C2—C3—H3A	121.4 (14)	O5—C14—C13	114.72 (17)
C4—C3—H3A	118.3 (14)	C14—C15—C10	122.06 (19)
C5—C4—C3	119.4 (2)	C14—C15—H15A	117.9 (12)
C5—C4—H4A	118.9 (15)	C10—C15—H15A	120.1 (12)
C3—C4—H4A	121.6 (14)	O3—C16—H16A	103.7 (14)
C4—C5—C6	122.0 (2)	O3—C16—H16B	111.0 (13)
C4—C5—H5A	117.5 (13)	H16A—C16—H16B	109 (2)
C6—C5—H5A	120.5 (13)	O3—C16—H16C	110.3 (14)
C5—C6—C1	117.40 (18)	H16A—C16—H16C	111.9 (18)
C5—C6—C7	123.12 (18)	H16B—C16—H16C	111 (2)
C1—C6—C7	119.48 (17)	O4—C17—H17A	110.4 (16)
O2—C7—C8	120.31 (18)	O4—C17—H17B	110.2 (14)
O2—C7—C6	120.05 (17)	H17A—C17—H17B	110 (2)
C8—C7—C6	119.61 (18)	O4—C17—H17C	106.8 (14)
C9—C8—C7	121.5 (2)	H17A—C17—H17C	111.1 (18)
C9—C8—H8A	121.7 (12)	H17B—C17—H17C	108 (2)
C7—C8—H8A	116.9 (12)	O5—C18—H18A	107.7 (13)
C8—C9—C10	127.1 (2)	O5—C18—H18B	112.3 (14)
C8—C9—H9A	115.3 (13)	H18A—C18—H18B	109.8 (17)
C10—C9—H9A	117.5 (13)	O5—C18—H18C	110.9 (13)
C11—C10—C15	117.57 (18)	H18A—C18—H18C	107 (2)
C11—C10—C9	120.77 (18)	H18B—C18—H18C	109.4 (19)
C15—C10—C9	121.66 (18)

O1—C1—C2—C3	176.7 (2)	C16—O3—C11—C10	178.07 (19)
C6—C1—C2—C3	−3.1 (3)	C15—C10—C11—O3	−178.60 (18)
C1—C2—C3—C4	0.0 (3)	C9—C10—C11—O3	0.9 (3)
C2—C3—C4—C5	2.2 (3)	C15—C10—C11—C12	0.5 (3)
C3—C4—C5—C6	−1.4 (3)	C9—C10—C11—C12	179.9 (2)
C4—C5—C6—C1	−1.6 (3)	O3—C11—C12—C13	179.56 (19)
C4—C5—C6—C7	177.9 (2)	C10—C11—C12—C13	0.6 (3)
O1—C1—C6—C5	−176.0 (2)	C17—O4—C13—C12	−2.5 (3)
C2—C1—C6—C5	3.9 (3)	C17—O4—C13—C14	177.65 (18)
O1—C1—C6—C7	4.4 (3)	C11—C12—C13—O4	179.0 (2)
C2—C1—C6—C7	−175.7 (2)	C11—C12—C13—C14	−1.2 (3)
C5—C6—C7—O2	168.3 (2)	C18—O5—C14—C15	3.1 (3)
C1—C6—C7—O2	−12.2 (3)	C18—O5—C14—C13	−176.94 (19)
C5—C6—C7—C8	−13.8 (3)	O4—C13—C14—C15	−179.32 (19)
C1—C6—C7—C8	165.8 (2)	C12—C13—C14—C15	0.9 (3)
O2—C7—C8—C9	−8.8 (3)	O4—C13—C14—O5	0.7 (3)
C6—C7—C8—C9	173.2 (2)	C12—C13—C14—O5	−179.08 (19)
C7—C8—C9—C10	179.7 (2)	O5—C14—C15—C10	−179.87 (19)
C8—C9—C10—C11	−176.5 (2)	C13—C14—C15—C10	0.2 (3)
C8—C9—C10—C15	2.9 (3)	C11—C10—C15—C14	−0.8 (3)
C16—O3—C11—C12	−1.0 (3)	C9—C10—C15—C14	179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.89 (3)	1.73 (3)	2.541 (2)	152 (2)
C5—H5A···O5ⁱ	0.96 (2)	2.57 (2)	3.254 (3)	129.0 (18)
C16—H16C···O1ⁱⁱ	1.04 (3)	2.42 (3)	3.446 (3)	167.5 (18)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₅
M_r	314.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	4.2891 (2), 17.3341 (9), 20.5732 (10)
V (Å³)	1529.57 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.56 × 0.16 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.946, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	16077, 2392, 1946
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.095, 1.08
No. of reflections	2392
No. of parameters	280
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20

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
O1—H1O1···O2	0.89 (3)	1.73 (3)	2.541 (2)	152 (2)
C5—H5A···O5ⁱ	0.96 (2)	2.57 (2)	3.254 (3)	129.0 (18)
C16—H16C···O1ⁱⁱ	1.04 (3)	2.42 (3)	3.446 (3)	167.5 (18)

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x, y−1/2, −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 (grant No. 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. KC thanks the Crystal Materials Research Unit, Prince of Songkla University, for a Research Assistance fellowship.

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