(E)-3-(4-Eth­oxy­phen­yl)-1-(2-hy­droxy­phen­yl)prop-2-en-1-one

Horkaew, J.; Chantrapromma, S.; Saewan, N.; Fun, H.-K.

doi:10.1107/S1600536810032514

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2346-o2347

https://doi.org/10.1107/S1600536810032514

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(E)-3-(4-Ethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

Jirapa Horkaew,^a Suchada Chantrapromma,^a ^*‡ Nisakorn Saewan ^b and Hoong-Kun Fun ^c §

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bSchool of Cosmetic Science, Mae Fah Luang University, Muang, Chiang Rai 57100, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 28 July 2010; accepted 12 August 2010; online 18 August 2010)

In the title compound, C₁₇H₁₆O₃, the carbonyl group is in an s-cis configuration with respect to the olefinic double bond. The dihedral angle between the two benzene rings is 2.85 (3)°. The prop-2-en-1-one bridge makes dihedral angles of 4.77 (4) and 4.15 (4)°, respectively, with the 2-hydroxyphenyl and 4-ethoxyphenyl rings. The ethoxy group is coplanar with the attached phenyl ring [C_ar—O—C—C = 179.72 (5)°]. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, molecules are stacked in an antiparallel manner to form columns along the b axis. The columnar structure is stabilized by C—H⋯π interactions involving the 2-hydroxyphenyl ring.

Related literature

For background on the applications of chalcones, see: Jun et al. (2007 ); Nowakowska (2007 ); Patil & Dharmaprakash (2008 ); Saydam et al. (2003 ); Svetlichny et al. (2007 ); Tewtrakul et al. (2003 ). 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. (2008 ); Patil et al. (2007 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₁₆O₃
M_r = 268.30
Triclinic, $[P \overline 1]$
a = 6.8305 (2) Å
b = 6.8790 (2) Å
c = 14.8188 (3) Å
α = 88.533 (1)°
β = 80.380 (1)°
γ = 77.469 (1)°
V = 670.11 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.60 × 0.38 × 0.36 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.948, T_max = 0.969
24772 measured reflections
5849 independent reflections
5179 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.124
S = 1.04
5848 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.93 (2)	1.66 (2)	2.5113 (7)	151 (1)
C16—H16A⋯Cg1ⁱ	0.97	2.70	3.5762 (7)	151
C16—H16B⋯Cg1ⁱⁱ	0.97	2.66	3.5339 (7)	151
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+2, -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/S1600536810032514/ci5143sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032514/ci5143Isup2.hkl

checkCIF report

Comment top

Chalcones is an interesting class of compounds which have been reported to posses various useful properties such as non-linear optical (NLO) (Patil & Dharmaprakash, 2008) and fluorescent properties (Svetlichny et al., 2007). Synthetic and naturally occurring chalcones have been found to exhibit many useful biological activities, including anti-inflammatory, antileishmanial, antimicrobial, antioxidant (Nowakowska, 2007; Saydam et al., 2003), HIV-1 protease inhibitory (Tewtrakul et al., 2003) and tyrosinase inhibitory (Jun et al., 2007) activities. Our on going research on NLO properties and bioactivities of the synthetic chalcones led us to synthesize the title chalcone in order to study its NLO properties, antibacterial and tyrosinase inhibitory activities. The results show that the title compound, (I), crystallized in centrosymmetric P1 space group which prohibits the second order NLO properties. Our biological testing found that (I) was inactive against the tested bacteria which are Gram-positive bacteria i.e. Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Methicillin-Resistant Staphylococcus aureus and Vancomycin-Resistant Enterococcus faecalis and Gram-negative bacteria i.e. Pseudomonas aeruginosa, Salmonella typhi and Shigella sonnei. Nevertheless (I) shows moderate tyrosinase inhibitory activity which will be reported elsewhere with some other chalcones. Herein the crystal structure of (I) is reported.

The title molecule (Fig. 1) exists in an E configuration with respect to the C8═C9 ethenyl bond [1.3475 (8) Å]; the C7–C8–C9–C10 torsion angle is -178.73 (6)°. The molecule is almost planar with the dihedral angle between the 2-hydroxyphenyl and 4-ethoxyphenyl rings being 2.85 (3)°. The substituted ethoxy group is coplanar with the attached phenyl ring with the torsion angle C13–O3–C16–C17 = 179.72 (5)°. The prop-2-en-1-one unit (C7–C9/O1) is planar [r.m.s. deviation 0.0098 (1) Å] and the torsion angle O1–C7–C8–C9 being 3.15 (10)°. This bridge makes dihedral angles of 4.77 (4) and 4.15 (4)° with the 2-hydroxyphenyl and 4-ethoxyphenyl rings, respectively. Intramolecular O2—H1O2···O1 hydrogen bond generates an S(6) ring motif (Fig. 1) (Bernstein et al., 1995) which helps to stabilize the planarity of the chalcone skeleton. The bond distances are of normal values (Allen et al., 1987) and are comparable with those observed in related structures (Fun et al., 2008; Patil et al., 2007).

In the crystal packing, the molecules are stacked in an antiparallel manner into columns along the b axis (Fig. 2). This arrangement is stabilized by C—H···π interactions (Table 1) involving the hydroxy phenyl ring. In addition C···O short contacts [3.2894 (8)–3.4003 (9) Å] were also observed.

Related literature top

For background on the applications of chalcones, see: Jun et al. (2007); Nowakowska (2007); Patil & Dharmaprakash (2008); Saydam et al. (2003); Svetlichny et al. (2007); Tewtrakul et al. (2003). 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. (2008); Patil et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by the condensation of 4-ethoxycarboxaldehyde (0.30 g, 2 mmol) with 2-hydroxyacetophenone (0.24 ml, 2 mmol) in ethanol (40 ml) in the presence of 30% aqueous NaOH (5 ml) at room temperature. After stirring for 3 h, 20% H₂SO₄(aq) (5 ml) was added dropwise into the solution. After the reaction mixture was kept at room temperature for a day, a yellow solid appeared and was then collected by filtration, washed with acetone and dried in air. Yellow block-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from acetone by slow evaporation of the solvent at room temperature after several days (m.p. 387–388 K).

Structure description top

For background on the applications of chalcones, see: Jun et al. (2007); Nowakowska (2007); Patil & Dharmaprakash (2008); Saydam et al. (2003); Svetlichny et al. (2007); Tewtrakul et al. (2003). 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. (2008); Patil et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 and the atom-numbering scheme. Intramolecular O—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound viewed along the a axis, showing antiparallel stacked columns running along the b axis.

(E)-3-(4-Ethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₆O₃	Z = 2
M_r = 268.30	F(000) = 284
Triclinic, P1	D_x = 1.330 Mg m⁻³
Hall symbol: -P 1	Melting point = 387–388 K
a = 6.8305 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 6.8790 (2) Å	Cell parameters from 5849 reflections
c = 14.8188 (3) Å	θ = 1.4–35.0°
α = 88.533 (1)°	µ = 0.09 mm⁻¹
β = 80.380 (1)°	T = 100 K
γ = 77.469 (1)°	Block, yellow
V = 670.11 (3) Å³	0.60 × 0.38 × 0.36 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5849 independent reflections
Radiation source: sealed tube	5179 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 35.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.948, T_max = 0.969	k = −10→11
24772 measured reflections	l = −23→23

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) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0744P)² + 0.1118P] where P = (F_o² + 2F_c²)/3
5848 reflections	(Δ/σ)_max = 0.001
186 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₇H₁₆O₃	γ = 77.469 (1)°
M_r = 268.30	V = 670.11 (3) Å³
Triclinic, P1	Z = 2
a = 6.8305 (2) Å	Mo Kα radiation
b = 6.8790 (2) Å	µ = 0.09 mm⁻¹
c = 14.8188 (3) Å	T = 100 K
α = 88.533 (1)°	0.60 × 0.38 × 0.36 mm
β = 80.380 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5849 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5179 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.969	R_int = 0.020
24772 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.39 e Å⁻³
5848 reflections	Δρ_min = −0.44 e Å⁻³
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 > 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	1.46060 (7)	0.63044 (8)	0.13054 (3)	0.01858 (10)
O2	1.59166 (7)	0.61854 (8)	0.27959 (4)	0.01890 (11)
H1O2	1.589 (2)	0.614 (2)	0.2173 (11)	0.052 (4)*
O3	0.61756 (7)	0.84310 (8)	−0.23045 (3)	0.01749 (10)
C1	1.39580 (9)	0.65747 (9)	0.32040 (4)	0.01353 (11)
C2	1.35615 (10)	0.66707 (10)	0.41620 (4)	0.01724 (12)
H2A	1.4636	0.6474	0.4490	0.021*
C3	1.15843 (11)	0.70553 (11)	0.46221 (5)	0.02141 (13)
H3A	1.1333	0.7123	0.5258	0.026*
C4	0.99566 (11)	0.73437 (12)	0.41364 (5)	0.02221 (14)
H4A	0.8626	0.7594	0.4448	0.027*
C5	1.03359 (10)	0.72550 (10)	0.31877 (4)	0.01683 (12)
H5A	0.9248	0.7447	0.2869	0.020*
C6	1.23305 (9)	0.68816 (9)	0.26988 (4)	0.01237 (10)
C7	1.27920 (9)	0.67709 (9)	0.16865 (4)	0.01267 (10)
C8	1.11547 (9)	0.72198 (9)	0.11403 (4)	0.01350 (11)
H8A	0.9811	0.7630	0.1425	0.016*
C9	1.16056 (9)	0.70358 (9)	0.02217 (4)	0.01346 (11)
H9A	1.2972	0.6595	−0.0024	0.016*
C10	1.01927 (9)	0.74506 (9)	−0.04275 (4)	0.01229 (10)
C11	0.80665 (9)	0.79158 (9)	−0.01582 (4)	0.01357 (11)
H11A	0.7517	0.7999	0.0461	0.016*
C12	0.67867 (9)	0.82501 (9)	−0.08002 (4)	0.01398 (11)
H12A	0.5386	0.8566	−0.0611	0.017*
C13	0.75873 (9)	0.81164 (9)	−0.17369 (4)	0.01315 (10)
C14	0.96900 (9)	0.76806 (10)	−0.20234 (4)	0.01477 (11)
H14A	1.0233	0.7606	−0.2643	0.018*
C15	1.09656 (9)	0.73581 (9)	−0.13654 (4)	0.01429 (11)
H15A	1.2367	0.7074	−0.1555	0.017*
C16	0.68663 (9)	0.83005 (9)	−0.32736 (4)	0.01484 (11)
H16A	0.7685	0.6985	−0.3445	0.018*
H16B	0.7680	0.9278	−0.3465	0.018*
C17	0.49767 (11)	0.87050 (11)	−0.37121 (5)	0.01895 (12)
H17A	0.5358	0.8690	−0.4366	0.028*
H17B	0.4155	0.9986	−0.3514	0.028*
H17C	0.4217	0.7696	−0.3536	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.01206 (19)	0.0280 (3)	0.0151 (2)	−0.00354 (17)	−0.00144 (15)	−0.00028 (17)
O2	0.01199 (19)	0.0265 (2)	0.0186 (2)	−0.00291 (17)	−0.00501 (16)	−0.00171 (18)
O3	0.01373 (19)	0.0271 (3)	0.01164 (19)	−0.00273 (17)	−0.00437 (14)	0.00013 (16)
C1	0.0135 (2)	0.0129 (2)	0.0151 (2)	−0.00301 (18)	−0.00482 (18)	0.00005 (18)
C2	0.0209 (3)	0.0179 (3)	0.0145 (2)	−0.0041 (2)	−0.0076 (2)	0.00091 (19)
C3	0.0244 (3)	0.0268 (3)	0.0130 (2)	−0.0054 (2)	−0.0034 (2)	0.0009 (2)
C4	0.0174 (3)	0.0329 (4)	0.0149 (3)	−0.0044 (2)	−0.0001 (2)	0.0007 (2)
C5	0.0130 (2)	0.0228 (3)	0.0145 (2)	−0.0035 (2)	−0.00232 (19)	0.0006 (2)
C6	0.0120 (2)	0.0133 (2)	0.0122 (2)	−0.00281 (17)	−0.00315 (17)	0.00025 (17)
C7	0.0127 (2)	0.0131 (2)	0.0129 (2)	−0.00335 (17)	−0.00318 (17)	0.00039 (17)
C8	0.0128 (2)	0.0150 (2)	0.0130 (2)	−0.00247 (18)	−0.00374 (18)	−0.00015 (18)
C9	0.0138 (2)	0.0146 (2)	0.0129 (2)	−0.00401 (18)	−0.00363 (17)	0.00107 (18)
C10	0.0129 (2)	0.0128 (2)	0.0116 (2)	−0.00302 (17)	−0.00291 (17)	0.00046 (17)
C11	0.0136 (2)	0.0159 (2)	0.0113 (2)	−0.00358 (18)	−0.00181 (17)	0.00037 (17)
C12	0.0124 (2)	0.0167 (2)	0.0125 (2)	−0.00295 (18)	−0.00149 (17)	−0.00021 (18)
C13	0.0127 (2)	0.0145 (2)	0.0126 (2)	−0.00236 (18)	−0.00379 (17)	0.00019 (18)
C14	0.0134 (2)	0.0191 (3)	0.0111 (2)	−0.00229 (19)	−0.00181 (17)	−0.00019 (18)
C15	0.0122 (2)	0.0177 (3)	0.0124 (2)	−0.00208 (18)	−0.00191 (17)	−0.00048 (18)
C16	0.0169 (2)	0.0151 (2)	0.0129 (2)	−0.00269 (19)	−0.00430 (18)	0.00006 (18)
C17	0.0206 (3)	0.0204 (3)	0.0173 (3)	−0.0031 (2)	−0.0091 (2)	0.0003 (2)

Geometric parameters (Å, º) top

O1—C7	1.2491 (7)	C9—C10	1.4543 (8)
O2—C1	1.3452 (8)	C9—H9A	0.93
O2—H1O2	0.928 (16)	C10—C15	1.3998 (8)
O3—C13	1.3621 (7)	C10—C11	1.4078 (8)
O3—C16	1.4334 (7)	C11—C12	1.3791 (8)
C1—C2	1.4006 (9)	C11—H11A	0.93
C1—C6	1.4174 (8)	C12—C13	1.4019 (8)
C2—C3	1.3803 (10)	C12—H12A	0.93
C2—H2A	0.93	C13—C14	1.3960 (8)
C3—C4	1.3993 (10)	C14—C15	1.3957 (8)
C3—H3A	0.93	C14—H14A	0.93
C4—C5	1.3868 (9)	C15—H15A	0.93
C4—H4A	0.93	C16—C17	1.5102 (9)
C5—C6	1.4053 (8)	C16—H16A	0.97
C5—H5A	0.93	C16—H16B	0.97
C6—C7	1.4808 (8)	C17—H17A	0.96
C7—C8	1.4632 (8)	C17—H17B	0.96
C8—C9	1.3475 (8)	C17—H17C	0.96
C8—H8A	0.93

C1—O2—H1O2	105.5 (10)	C15—C10—C9	118.97 (5)
C13—O3—C16	118.56 (5)	C11—C10—C9	123.04 (5)
O2—C1—C2	117.49 (5)	C12—C11—C10	120.91 (5)
O2—C1—C6	122.28 (5)	C12—C11—H11A	119.5
C2—C1—C6	120.23 (6)	C10—C11—H11A	119.5
C3—C2—C1	120.32 (6)	C11—C12—C13	120.33 (5)
C3—C2—H2A	119.8	C11—C12—H12A	119.8
C1—C2—H2A	119.8	C13—C12—H12A	119.8
C2—C3—C4	120.34 (6)	O3—C13—C14	125.05 (5)
C2—C3—H3A	119.8	O3—C13—C12	114.98 (5)
C4—C3—H3A	119.8	C14—C13—C12	119.97 (5)
C5—C4—C3	119.71 (6)	C15—C14—C13	119.03 (5)
C5—C4—H4A	120.1	C15—C14—H14A	120.5
C3—C4—H4A	120.1	C13—C14—H14A	120.5
C4—C5—C6	121.34 (6)	C14—C15—C10	121.76 (5)
C4—C5—H5A	119.3	C14—C15—H15A	119.1
C6—C5—H5A	119.3	C10—C15—H15A	119.1
C5—C6—C1	118.06 (5)	O3—C16—C17	106.17 (5)
C5—C6—C7	122.80 (5)	O3—C16—H16A	110.5
C1—C6—C7	119.14 (5)	C17—C16—H16A	110.5
O1—C7—C8	120.46 (5)	O3—C16—H16B	110.5
O1—C7—C6	118.86 (5)	C17—C16—H16B	110.5
C8—C7—C6	120.67 (5)	H16A—C16—H16B	108.7
C9—C8—C7	119.61 (5)	C16—C17—H17A	109.5
C9—C8—H8A	120.2	C16—C17—H17B	109.5
C7—C8—H8A	120.2	H17A—C17—H17B	109.5
C8—C9—C10	127.21 (5)	C16—C17—H17C	109.5
C8—C9—H9A	116.4	H17A—C17—H17C	109.5
C10—C9—H9A	116.4	H17B—C17—H17C	109.5
C15—C10—C11	117.98 (5)

O2—C1—C2—C3	−179.69 (6)	C7—C8—C9—C10	−178.73 (5)
C6—C1—C2—C3	0.31 (10)	C8—C9—C10—C15	173.80 (6)
C1—C2—C3—C4	0.31 (11)	C8—C9—C10—C11	−7.18 (10)
C2—C3—C4—C5	−0.43 (12)	C15—C10—C11—C12	0.63 (9)
C3—C4—C5—C6	−0.06 (11)	C9—C10—C11—C12	−178.39 (5)
C4—C5—C6—C1	0.65 (10)	C10—C11—C12—C13	0.49 (9)
C4—C5—C6—C7	179.82 (6)	C16—O3—C13—C14	0.40 (9)
O2—C1—C6—C5	179.22 (6)	C16—O3—C13—C12	−179.35 (5)
C2—C1—C6—C5	−0.78 (9)	C11—C12—C13—O3	178.52 (5)
O2—C1—C6—C7	0.03 (9)	C11—C12—C13—C14	−1.24 (9)
C2—C1—C6—C7	−179.97 (5)	O3—C13—C14—C15	−178.90 (6)
C5—C6—C7—O1	−175.37 (6)	C12—C13—C14—C15	0.83 (9)
C1—C6—C7—O1	3.79 (9)	C13—C14—C15—C10	0.32 (10)
C5—C6—C7—C8	5.26 (9)	C11—C10—C15—C14	−1.04 (9)
C1—C6—C7—C8	−175.59 (5)	C9—C10—C15—C14	178.03 (6)
O1—C7—C8—C9	3.15 (9)	C13—O3—C16—C17	179.71 (5)
C6—C7—C8—C9	−177.48 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the O2,C1–C6 ring?

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.93 (2)	1.66 (2)	2.5113 (7)	151 (1)
C16—H16A···Cg1ⁱ	0.97	2.70	3.5762 (7)	151
C16—H16B···Cg1ⁱⁱ	0.97	2.66	3.5339 (7)	151

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₃
M_r	268.30
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.8305 (2), 6.8790 (2), 14.8188 (3)
α, β, γ (°)	88.533 (1), 80.380 (1), 77.469 (1)
V (Å³)	670.11 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.60 × 0.38 × 0.36

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.948, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	24772, 5849, 5179
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.124, 1.04
No. of reflections	5848
No. of parameters	186
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.44

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the O2,C1–C6 ring?

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.93 (2)	1.66 (2)	2.5113 (7)	151 (1)
C16—H16A···Cg1ⁱ	0.97	2.70	3.5762 (7)	151
C16—H16B···Cg1ⁱⁱ	0.97	2.66	3.5339 (7)	151

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

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

Acknowledgements

The authors thank the Thailand Research Fund (TRF) for the research grant (grant No. RSA 5280033) and the Prince of Songkla University for financial support. The authors also thank the Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University is acknowledged for the bacterial assay.

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