(E)-3-[4-(Dec­yloxy)phen­yl]-1-(4-hydroxy­phen­yl)prop-2-en-1-one

Razak, I.A.; Fun, H.-K.; Ngaini, Z.; Rahman, N.I.A.; Hussain, H.

doi:10.1107/S160053680901441X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages o1092-o1093

doi:10.1107/S160053680901441X

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(E)-3-[4-(Decyloxy)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one

Ibrahim Abdul Razak,^a ^*‡ Hoong-Kun Fun,^a § Zainab Ngaini,^b Norashikin Irdawaty Abd Rahman ^b and Hasnain Hussain ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and ^cDepartment of Molecular Biology, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 15 April 2009; accepted 17 April 2009; online 22 April 2009)

In the title compound, C₂₅H₃₂O₃, the enone group adopts an s–cis conformation. The alkoxy unit is nearly planar and is in a trans conformation. The two benzene rings make a dihedral angle of 18.87 (9)°. In the crystal structure, molecules are linked into chains running along the a axis by intermolecular O—H⋯O hydrogen bonds involving the hydroxy and keto groups. The chains are crosslinked along the b axis via C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the ab plane.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ); Xue et al. (2004 ); Satyanarayana et al. (2004 ); Lee et al. (2006 ). For related structures, see: Ng et al. (2006 ); Razak et al. (2009 ); Ngaini, Fadzillah et al. (2009 ); Ngaini, Rahman et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₅H₃₂O₃
M_r = 380.51
Orthorhombic, P b c a
a = 10.5192 (3) Å
b = 9.9839 (3) Å
c = 40.8415 (12) Å
V = 4289.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.58 × 0.49 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.957, T_max = 0.998
42832 measured reflections
4922 independent reflections
3526 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.132
S = 1.10
4922 reflections
258 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 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
O1—H1O1⋯O2ⁱ	0.95 (3)	1.71 (3)	2.655 (2)	177 (3)
C5—H5⋯O1ⁱⁱ	0.93	2.48	3.340 (2)	155
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S160053680901441X/ci2782sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901441X/ci2782Isup2.hkl

checkCIF report

Comment top

Chalcone derivatives possess a wide range of biological properties such as antimalarial (Xue et al., 2004), antiangiogenic and antitumour (Lee et al., 2006), anticancer (Bhat et al., 2005) and antihyperglycemic (Satyanarayana et al., 2004) activities. Chalcones have been widely studied and developed as one of the pharmaceutically important molecules. We have synthesized the title chalcone derivative and tested and confirmed its activities against E. coli ATCC 8739. As part of our studies on chalcone derivatives, we report here the crystal structure of the title compound.

In the title molecule (Fig 1), bond lengths show normal values (Allen et al., 1987). The mean plane through the enone moiety (O2/C7/C8/C9) form dihedral angles of 19.26 (12)° and 2.14 (12)°, respectively, with the C1-C6 and C10-C15 benzene rings. The dihedral angle between the two benzene rings is 18.87 (9)°. The conformation of the enone moiety is s-cis with O2—C7—C8—C9 torsion angle being 5.4 (3)°. Slight enlargement of C5—C6—C7 (122.43 (18)°) angle is as a result of the short H5···H8 (2.18 Å) contact whereas short H8···H11 (2.30 Å) contact widened the C8—C9—C10 (128.13 (19)°) and C9—C10—C11 (123.63 (18)°) angles. Similarly, strain induced by close interatomic contact between H14 and H16A (2.27 Å) resulted in the opening of O3—C13—C14 (124.86 (17)°) angle. Related structures by Ng et al.(2006), Razak et al. (2009), Ngaini, Fadzillah et al. (2009) and Ngaini, Rahman et al. (2009) have also reported similar features.

The zigzag alkoxyl tail adopts a trans conformation with the largest deviation from the ideal value being 175.44 (17)° for C17—C18—C19—C20 torsion angle. The alkoxyl chain (O3/C16-C25) is nearly planar with the maximum deviation from the least-squares plane being 0.116 (1) Å for atom C19. The dihedral angle between the O3/C16-C25 and C10-C15 planes is 6.29 (13)°.

In the crystal structure, the molecules are arranged in alternating head-to-head zigzag layers along the c axis (Fig. 2). Intermolecular O1—H1O1···O2(x + 1/2,y,-z + 1/2) hydrogen bonds (Table 1) between hydroxy and keto groups form extended chains along the a axis. These chains are interconnected along the b axis by C5—H5···O1(-x + 2,y - 1/2,-z + 1/2) intermolecular interactions forming a two-dimensional network parallel to the ab plane.

Related literature top

For the biological properties of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004); Satyanarayana et al. (2004); Lee et al. (2006). For related structures, see: Ng et al. (2006); Razak et al. (2009); Ngaini, Fadzillah et al. (2009); Ngaini, Rahman et al. (2009). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 4-hydroxyacetophenone (2.72 g, 20 mmol) and 4-decyloxybenzaldehyde (5.25 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in methanol (60 ml) was heated at reflux for 24 h. The reaction mixture was cooled to room temperature and acidified with cold diluted HCl (2 N). The resulting precipitate was filtered, washed and dried. After redissolving in a hexane-ethanol (7:1) solution, followed by few days of slow evaporation, crystals were collected.

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.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds.

(E)-3-[4-(Decyloxy)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one top

Crystal data top

C₂₅H₃₂O₃	F(000) = 1648
M_r = 380.51	D_x = 1.178 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4176 reflections
a = 10.5192 (3) Å	θ = 2.2–23.9°
b = 9.9839 (3) Å	µ = 0.08 mm⁻¹
c = 40.8415 (12) Å	T = 100 K
V = 4289.3 (2) Å³	Plate, colourless
Z = 8	0.58 × 0.49 × 0.03 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4922 independent reflections
Radiation source: sealed tube	3526 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
π and ω scans	θ_max = 27.5°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.957, T_max = 0.998	k = −12→12
42832 measured reflections	l = −53→52

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0368P)² + 2.6345P] where P = (F_o² + 2F_c²)/3
4922 reflections	(Δ/σ)_max = 0.001
258 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₅H₃₂O₃	V = 4289.3 (2) Å³
M_r = 380.51	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.5192 (3) Å	µ = 0.08 mm⁻¹
b = 9.9839 (3) Å	T = 100 K
c = 40.8415 (12) Å	0.58 × 0.49 × 0.03 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4922 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3526 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.998	R_int = 0.082
42832 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.20 e Å⁻³
4922 reflections	Δρ_min = −0.22 e Å⁻³
258 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 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	0.97999 (14)	0.70636 (15)	0.20018 (3)	0.0232 (3)
O2	0.66825 (13)	0.56794 (14)	0.32684 (3)	0.0228 (3)
O3	0.93786 (13)	−0.03516 (14)	0.45190 (3)	0.0227 (3)
C1	0.79176 (18)	0.6934 (2)	0.27426 (5)	0.0213 (4)
H1	0.7242	0.7397	0.2836	0.026*
C2	0.83983 (19)	0.7353 (2)	0.24449 (5)	0.0220 (4)
H2	0.8051	0.8096	0.2340	0.026*
C3	0.94058 (19)	0.6659 (2)	0.23015 (5)	0.0198 (4)
C4	0.9958 (2)	0.5589 (2)	0.24676 (5)	0.0224 (4)
H4	1.0655	0.5149	0.2378	0.027*
C5	0.94723 (18)	0.5179 (2)	0.27665 (5)	0.0219 (4)
H5	0.9847	0.4463	0.2875	0.026*
C6	0.84262 (18)	0.5826 (2)	0.29070 (4)	0.0193 (4)
C7	0.77760 (18)	0.5307 (2)	0.32020 (4)	0.0189 (4)
C8	0.84031 (19)	0.4306 (2)	0.34137 (4)	0.0206 (4)
H8	0.9248	0.4078	0.3377	0.025*
C9	0.77621 (19)	0.3725 (2)	0.36590 (4)	0.0204 (4)
H9	0.6932	0.4018	0.3690	0.024*
C10	0.82043 (18)	0.2687 (2)	0.38841 (4)	0.0204 (4)
C11	0.94097 (18)	0.2090 (2)	0.38649 (5)	0.0216 (4)
H11	0.9981	0.2378	0.3706	0.026*
C12	0.97590 (19)	0.1086 (2)	0.40773 (5)	0.0222 (5)
H12	1.0560	0.0698	0.4059	0.027*
C13	0.89207 (19)	0.0645 (2)	0.43198 (4)	0.0201 (4)
C14	0.77209 (18)	0.1205 (2)	0.43435 (5)	0.0213 (4)
H14	0.7153	0.0914	0.4503	0.026*
C15	0.73770 (19)	0.2212 (2)	0.41247 (4)	0.0223 (4)
H15	0.6567	0.2581	0.4139	0.027*
C16	0.85615 (19)	−0.0838 (2)	0.47766 (5)	0.0223 (5)
H16A	0.7759	−0.1141	0.4686	0.027*
H16B	0.8391	−0.0130	0.4933	0.027*
C17	0.92412 (19)	−0.1985 (2)	0.49413 (5)	0.0226 (5)
H17A	1.0055	−0.1674	0.5023	0.027*
H17B	0.9403	−0.2684	0.4782	0.027*
C18	0.84727 (19)	−0.2561 (2)	0.52231 (5)	0.0241 (5)
H18A	0.7647	−0.2837	0.5142	0.029*
H18B	0.8337	−0.1867	0.5386	0.029*
C19	0.91156 (19)	−0.3754 (2)	0.53860 (5)	0.0245 (5)
H19A	0.9968	−0.3496	0.5451	0.029*
H19B	0.9190	−0.4472	0.5227	0.029*
C20	0.84121 (19)	−0.4277 (2)	0.56855 (5)	0.0246 (5)
H20A	0.8313	−0.3552	0.5842	0.030*
H20B	0.7569	−0.4565	0.5620	0.030*
C21	0.9087 (2)	−0.5439 (2)	0.58526 (5)	0.0260 (5)
H21A	0.9129	−0.6187	0.5701	0.031*
H21B	0.9951	−0.5172	0.5903	0.031*
C22	0.8444 (2)	−0.5903 (2)	0.61656 (5)	0.0282 (5)
H22A	0.8427	−0.5161	0.6319	0.034*
H22B	0.7570	−0.6136	0.6116	0.034*
C23	0.90728 (19)	−0.7093 (2)	0.63310 (5)	0.0266 (5)
H23A	0.9130	−0.7823	0.6175	0.032*
H23B	0.9932	−0.6846	0.6393	0.032*
C24	0.8373 (2)	−0.7579 (2)	0.66318 (5)	0.0347 (6)
H24A	0.7505	−0.7799	0.6572	0.042*
H24B	0.8342	−0.6861	0.6792	0.042*
C25	0.8993 (2)	−0.8805 (3)	0.67877 (6)	0.0446 (7)
H25A	0.8492	−0.9095	0.6971	0.067*
H25B	0.9833	−0.8577	0.6861	0.067*
H25C	0.9043	−0.9513	0.6629	0.067*
H1O1	1.046 (3)	0.654 (3)	0.1909 (7)	0.078 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0271 (8)	0.0216 (8)	0.0209 (7)	0.0019 (7)	0.0033 (6)	0.0032 (6)
O2	0.0224 (7)	0.0248 (8)	0.0213 (7)	0.0034 (7)	0.0014 (6)	0.0005 (6)
O3	0.0228 (7)	0.0231 (8)	0.0222 (7)	0.0004 (6)	0.0017 (6)	0.0052 (6)
C1	0.0207 (10)	0.0187 (11)	0.0245 (10)	0.0008 (9)	0.0005 (8)	−0.0032 (9)
C2	0.0230 (10)	0.0175 (11)	0.0255 (11)	0.0006 (9)	0.0002 (8)	0.0024 (9)
C3	0.0239 (10)	0.0159 (11)	0.0195 (10)	−0.0047 (9)	−0.0001 (8)	0.0004 (8)
C4	0.0239 (10)	0.0195 (11)	0.0237 (10)	0.0032 (9)	0.0025 (8)	−0.0016 (9)
C5	0.0235 (10)	0.0186 (11)	0.0236 (10)	0.0005 (9)	−0.0006 (8)	0.0010 (9)
C6	0.0212 (10)	0.0169 (11)	0.0198 (10)	−0.0021 (9)	−0.0010 (8)	−0.0018 (8)
C7	0.0226 (10)	0.0152 (10)	0.0190 (10)	−0.0001 (9)	−0.0018 (8)	−0.0048 (8)
C8	0.0203 (10)	0.0213 (11)	0.0203 (10)	0.0004 (9)	−0.0006 (8)	−0.0017 (8)
C9	0.0228 (10)	0.0205 (11)	0.0178 (10)	−0.0004 (9)	−0.0012 (8)	−0.0029 (8)
C10	0.0231 (10)	0.0208 (11)	0.0171 (9)	−0.0012 (9)	−0.0002 (8)	−0.0028 (8)
C11	0.0222 (10)	0.0246 (12)	0.0178 (10)	−0.0032 (9)	0.0008 (8)	0.0019 (9)
C12	0.0187 (10)	0.0265 (12)	0.0215 (10)	0.0000 (9)	0.0002 (8)	−0.0016 (9)
C13	0.0238 (10)	0.0187 (11)	0.0179 (9)	−0.0012 (9)	−0.0023 (8)	0.0002 (8)
C14	0.0223 (10)	0.0199 (11)	0.0216 (10)	−0.0029 (9)	0.0038 (8)	0.0011 (9)
C15	0.0213 (10)	0.0235 (12)	0.0221 (10)	0.0021 (9)	0.0005 (8)	−0.0017 (9)
C16	0.0249 (10)	0.0212 (11)	0.0207 (10)	−0.0017 (9)	0.0021 (8)	0.0030 (8)
C17	0.0224 (10)	0.0209 (11)	0.0245 (10)	−0.0031 (9)	−0.0022 (8)	−0.0002 (9)
C18	0.0260 (10)	0.0233 (12)	0.0230 (10)	−0.0006 (10)	−0.0015 (8)	0.0036 (9)
C19	0.0279 (11)	0.0223 (12)	0.0234 (10)	0.0014 (10)	0.0018 (9)	0.0011 (9)
C20	0.0249 (11)	0.0235 (12)	0.0255 (11)	−0.0018 (10)	−0.0006 (9)	0.0032 (9)
C21	0.0272 (11)	0.0249 (12)	0.0261 (11)	0.0006 (10)	0.0009 (9)	0.0037 (9)
C22	0.0261 (11)	0.0269 (12)	0.0315 (12)	0.0029 (10)	0.0007 (9)	0.0071 (10)
C23	0.0260 (11)	0.0270 (12)	0.0268 (11)	0.0001 (10)	0.0005 (9)	0.0046 (9)
C24	0.0357 (13)	0.0337 (14)	0.0346 (12)	0.0097 (12)	0.0066 (10)	0.0125 (10)
C25	0.0445 (15)	0.0485 (17)	0.0408 (14)	0.0177 (13)	0.0110 (12)	0.0201 (13)

Geometric parameters (Å, º) top

O1—C3	1.354 (2)	C16—C17	1.508 (3)
O1—H1O1	0.94 (3)	C16—H16A	0.97
O2—C7	1.239 (2)	C16—H16B	0.97
O3—C13	1.373 (2)	C17—C18	1.520 (3)
O3—C16	1.443 (2)	C17—H17A	0.97
C1—C2	1.382 (3)	C17—H17B	0.97
C1—C6	1.400 (3)	C18—C19	1.522 (3)
C1—H1	0.93	C18—H18A	0.97
C2—C3	1.395 (3)	C18—H18B	0.97
C2—H2	0.93	C19—C20	1.522 (3)
C3—C4	1.392 (3)	C19—H19A	0.97
C4—C5	1.385 (3)	C19—H19B	0.97
C4—H4	0.93	C20—C21	1.522 (3)
C5—C6	1.399 (3)	C20—H20A	0.97
C5—H5	0.93	C20—H20B	0.97
C6—C7	1.479 (3)	C21—C22	1.518 (3)
C7—C8	1.477 (3)	C21—H21A	0.97
C8—C9	1.340 (3)	C21—H21B	0.97
C8—H8	0.93	C22—C23	1.518 (3)
C9—C10	1.461 (3)	C22—H22A	0.97
C9—H9	0.93	C22—H22B	0.97
C10—C15	1.396 (3)	C23—C24	1.513 (3)
C10—C11	1.403 (3)	C23—H23A	0.97
C11—C12	1.376 (3)	C23—H23B	0.97
C11—H11	0.93	C24—C25	1.526 (3)
C12—C13	1.397 (3)	C24—H24A	0.97
C12—H12	0.93	C24—H24B	0.97
C13—C14	1.384 (3)	C25—H25A	0.96
C14—C15	1.393 (3)	C25—H25B	0.96
C14—H14	0.93	C25—H25C	0.96
C15—H15	0.93

C3—O1—H1O1	115.1 (18)	C16—C17—H17A	109.2
C13—O3—C16	117.84 (15)	C18—C17—H17A	109.2
C2—C1—C6	121.44 (19)	C16—C17—H17B	109.2
C2—C1—H1	119.3	C18—C17—H17B	109.2
C6—C1—H1	119.3	H17A—C17—H17B	107.9
C1—C2—C3	119.77 (19)	C17—C18—C19	113.01 (17)
C1—C2—H2	120.1	C17—C18—H18A	109.0
C3—C2—H2	120.1	C19—C18—H18A	109.0
O1—C3—C4	122.77 (18)	C17—C18—H18B	109.0
O1—C3—C2	117.63 (18)	C19—C18—H18B	109.0
C4—C3—C2	119.60 (18)	H18A—C18—H18B	107.8
C5—C4—C3	120.12 (19)	C18—C19—C20	113.81 (17)
C5—C4—H4	119.9	C18—C19—H19A	108.8
C3—C4—H4	119.9	C20—C19—H19A	108.8
C4—C5—C6	121.03 (19)	C18—C19—H19B	108.8
C4—C5—H5	119.5	C20—C19—H19B	108.8
C6—C5—H5	119.5	H19A—C19—H19B	107.7
C5—C6—C1	117.92 (18)	C21—C20—C19	113.30 (17)
C5—C6—C7	122.43 (18)	C21—C20—H20A	108.9
C1—C6—C7	119.38 (17)	C19—C20—H20A	108.9
O2—C7—C8	119.34 (17)	C21—C20—H20B	108.9
O2—C7—C6	120.14 (18)	C19—C20—H20B	108.9
C8—C7—C6	120.48 (17)	H20A—C20—H20B	107.7
C9—C8—C7	120.40 (18)	C22—C21—C20	113.74 (17)
C9—C8—H8	119.8	C22—C21—H21A	108.8
C7—C8—H8	119.8	C20—C21—H21A	108.8
C8—C9—C10	128.13 (19)	C22—C21—H21B	108.8
C8—C9—H9	115.9	C20—C21—H21B	108.8
C10—C9—H9	115.9	H21A—C21—H21B	107.7
C15—C10—C11	117.26 (18)	C23—C22—C21	114.78 (17)
C15—C10—C9	119.05 (18)	C23—C22—H22A	108.6
C11—C10—C9	123.63 (18)	C21—C22—H22A	108.6
C12—C11—C10	121.05 (18)	C23—C22—H22B	108.6
C12—C11—H11	119.5	C21—C22—H22B	108.6
C10—C11—H11	119.5	H22A—C22—H22B	107.5
C11—C12—C13	120.53 (19)	C24—C23—C22	113.59 (18)
C11—C12—H12	119.7	C24—C23—H23A	108.8
C13—C12—H12	119.7	C22—C23—H23A	108.8
O3—C13—C14	124.86 (17)	C24—C23—H23B	108.8
O3—C13—C12	115.28 (17)	C22—C23—H23B	108.8
C14—C13—C12	119.86 (18)	H23A—C23—H23B	107.7
C13—C14—C15	118.92 (18)	C23—C24—C25	112.84 (19)
C13—C14—H14	120.5	C23—C24—H24A	109.0
C15—C14—H14	120.5	C25—C24—H24A	109.0
C14—C15—C10	122.36 (19)	C23—C24—H24B	109.0
C14—C15—H15	118.8	C25—C24—H24B	109.0
C10—C15—H15	118.8	H24A—C24—H24B	107.8
O3—C16—C17	107.35 (15)	C24—C25—H25A	109.5
O3—C16—H16A	110.2	C24—C25—H25B	109.5
C17—C16—H16A	110.2	H25A—C25—H25B	109.5
O3—C16—H16B	110.2	C24—C25—H25C	109.5
C17—C16—H16B	110.2	H25A—C25—H25C	109.5
H16A—C16—H16B	108.5	H25B—C25—H25C	109.5
C16—C17—C18	111.91 (17)

C6—C1—C2—C3	0.5 (3)	C9—C10—C11—C12	−177.86 (19)
C1—C2—C3—O1	176.56 (18)	C10—C11—C12—C13	−0.6 (3)
C1—C2—C3—C4	−3.1 (3)	C16—O3—C13—C14	−1.2 (3)
O1—C3—C4—C5	−176.75 (18)	C16—O3—C13—C12	179.30 (17)
C2—C3—C4—C5	2.9 (3)	C11—C12—C13—O3	−179.39 (17)
C3—C4—C5—C6	−0.1 (3)	C11—C12—C13—C14	1.1 (3)
C4—C5—C6—C1	−2.5 (3)	O3—C13—C14—C15	−179.93 (18)
C4—C5—C6—C7	171.60 (18)	C12—C13—C14—C15	−0.5 (3)
C2—C1—C6—C5	2.3 (3)	C13—C14—C15—C10	−0.7 (3)
C2—C1—C6—C7	−171.99 (18)	C11—C10—C15—C14	1.2 (3)
C5—C6—C7—O2	−160.79 (19)	C9—C10—C15—C14	178.62 (19)
C1—C6—C7—O2	13.2 (3)	C13—O3—C16—C17	175.86 (16)
C5—C6—C7—C8	17.0 (3)	O3—C16—C17—C18	178.90 (16)
C1—C6—C7—C8	−168.94 (18)	C16—C17—C18—C19	177.92 (17)
O2—C7—C8—C9	5.4 (3)	C17—C18—C19—C20	175.44 (17)
C6—C7—C8—C9	−172.41 (18)	C18—C19—C20—C21	−178.11 (18)
C7—C8—C9—C10	177.52 (18)	C19—C20—C21—C22	175.79 (18)
C8—C9—C10—C15	−179.9 (2)	C20—C21—C22—C23	177.99 (18)
C8—C9—C10—C11	−2.7 (3)	C21—C22—C23—C24	−176.90 (19)
C15—C10—C11—C12	−0.6 (3)	C22—C23—C24—C25	178.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	0.95 (3)	1.71 (3)	2.655 (2)	177 (3)
C5—H5···O1ⁱⁱ	0.93	2.48	3.340 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₂₅H₃₂O₃
M_r	380.51
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	10.5192 (3), 9.9839 (3), 40.8415 (12)
V (Å³)	4289.3 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.58 × 0.49 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.957, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	42832, 4922, 3526
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.132, 1.10
No. of reflections	4922
No. of parameters	258
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −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
O1—H1O1···O2ⁱ	0.95 (3)	1.71 (3)	2.655 (2)	177 (3)
C5—H5···O1ⁱⁱ	0.93	2.48	3.340 (2)	155

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

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

Acknowledgements

HKF and IAR thank the Malaysian government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312 and for Research University Golden Goose grant No. 1001/PFIZIK/811012. ZN and HH thank Universiti Malaysia Sarawak for Geran Penyelidikan Dana Khas Inovasi grant No. DI/01/2007(01). NIAR thanks the Malaysian government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.

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