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

Ngaini, Z.; Fadzillah, S.M.H.; Hussain, H.; Razak, I.A.; Fun, H.-K.

doi:10.1107/S1600536809017577

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1301-o1302

doi:10.1107/S1600536809017577

Open

access

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

Zainab Ngaini,^a Siti Muhaini Haris Fadzillah,^a Hasnain Hussain,^b Ibrahim Abdul Razak ^c ^*‡ and Hoong-Kun Fun ^c §

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

(Received 7 May 2009; accepted 11 May 2009; online 14 May 2009)

In the title compound, C₂₁H₂₄O₃, the conformation of the enone group is s–cis. The benzene rings are inclined at an angle of 7.9 (1)°. The alkoxy tail is planar, with a maximum deviation from the least-squares plane of 0.009 (2) Å, and adopts a trans conformation throughout. An intramolecular O—H⋯O interaction between the keto and hydroxy groups forms S(6) ring motifs. In the crystal, molecules are arranged in a head-to-tail manner down the a axis and are subsequently stacked along the b axis, forming molecular sheets parallel to the ab plane. The crystal structure is further stabilized by weak C—H⋯π interactions and short C⋯O [3.376 (2) Å] contacts.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ); Xue et al. (2004 ); Zhao et al. (2005 ); Lee et al. (2006 ). For related structures, see: Razak, Fun, Ngaini, Rahman & Hussain (2009 ); Razak, Fun, Ngaini, Fadzillah & Hussain (2009a ,b ); Ngaini, Fadzillah et al. (2009 ); Ngaini, Rahman et al. (2009 ). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₂₄O₃
M_r = 324.40
Monoclinic, P 2₁ /c
a = 19.6443 (5) Å
b = 7.1966 (2) Å
c = 12.6520 (3) Å
β = 106.438 (2)°
V = 1715.53 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.47 × 0.12 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.962, T_max = 0.997
20873 measured reflections
5025 independent reflections
2783 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.190
S = 1.05
5025 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.90 (3)	1.68 (3)	2.507 (2)	152 (2)
C20—H20A⋯Cg1ⁱ	0.97	2.84	3.657 (2)	142
C20—H20B⋯Cg1ⁱⁱ	0.97	2.78	3.637 (2)	147
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C1-C6 ring.

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/S1600536809017577/sj2623sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809017577/sj2623Isup2.hkl

checkCIF report

Comment top

The biological properties of chalcones derivatives, such as their anticancer (Bhat et al., 2005), antimalarial (Xue et al., 2004), antiangiogenic and antitumour (Lee et al., 2006) and antiplatelet (Zhao et al., 2005) activities, have been extensively reported. Synthetic and naturally occurring chalcones are of interest and have been widely studied and developed as one of the pharmaceutically important molecules. As part of our studies, we have synthesized the title chalcone derivative, (I). Its antibacterial activity was tested against E. coli ATCC 8739 and the compound demonstrated antimicrobial activity. In this paper, we report the crystal structure of the title compound.

The bond lengths observed in the title compound (Fig.1) are comparable with those reported by Allen et al. (1987). The enone (O2/C7—C9) moiety adopts s-cis conformation with a O2—C7—C8—C9 torsion angle of -3.6 (3)°. The mean plane through the enone moiety makes dihedral angles of 0.89 (1)° and 7.9 (1)° with the C1—C6 and C10—C15 benzene rings, respectively. The dihedral angle between the two benzene rings is 7.9 (1)°.

The slight opening of the C1—C6—C7 (123.4 (2)°) and C6—C7—C8 (121.1 (2)°) angles is the result of the short H1A···H8A (2.15 Å) contact whereas close interatomic contact between H8A and H15A (2.36 Å) widened the C8—C9—C10 and C9—C10—C15 angles to 129.2 (2)° and 124.1 (2)°, respectively. Likewise, strain induced by short H12A···H16A (2.39 Å) and H12A···H16B (2.33 Å) contacts resulted in the opening of the O3—C13—C12 (125.1 (2)°) angle. Similar features were also reported in related structures (Razak, Fun, Ngaini, Rahman et al., 2009; Razak, Fun, Ngaini, Fadzillah & Hussain, 2009a,b; Ngaini, Fadzillah et al., 2009; Ngaini, Rahman et al., 2009).

The zigzag alkoxyl tail adopts an all-trans conformation with the largest deviation from the ideal value being -179.3 (2)° for C17—C18—C19—C20 torsion angle. The alkoxyl chain is planar with the maximum deviation from the least-squares plane of 0.009 (2)Å at C18. The zigzag plane makes a dihedral angle of 2.2 (1)° with the attached benzene ring.

The keto and hydroxy groups in the molecule form an intramolecular O1—H1O1···O2 interaction (Table 1) generating a ring of graph-set motif S(6) (Bernstein et al., 1995). In the crystal structure, the molecules are arranged into a head-to-tail manner down the a axis (Fig. 2). Molecules are subsequently stacked along the b axis, forming molecular sheets parallel to the ab plane. In the absence of conventional hydrogen bonds, the crystal packing is strengthened by the presence of weak C—H···π interactions between atom C20 of the alkoxyl tail and the C1—C6 benzene ring (Table 1). There is also a short C···O (x, 1.5-y, 0.5+z ) [3.376 (2)Å] contact.

Related literature top

For the biological properties of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004); Zhao et al. (2005); Lee et al. (2006). For related structures, see: Razak, Fun, Ngaini, Rahman & Hussain (2009); Razak, Fun, Ngaini, Fadzillah & Hussain (2009a,b); Ngaini, Fadzillah et al. (2009); Ngaini, Rahman et al. (2009) For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of the C1-C6 ring.

Experimental top

A mixture of 2-hydroxyacetophenone (2.72 ml, 20 mmol) and 4-hexyloxybenzaldehyde (4.12 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in 60 ml of methanol was heated at reflux for 24 h. The reaction was cooled to room temperature and acidified with cold diluted HCl (2 M). The resulting precipitate was filtered, washed and dried. After redissolving in hexane, 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. The intramolecular interaction is shown as dashed line.
	Fig. 2. The crystal packing of the title compound, viewed down the c axis.

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

Crystal data top

C₂₁H₂₄O₃	F(000) = 696
M_r = 324.40	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3217 reflections
a = 19.6443 (5) Å	θ = 3.0–30.0°
b = 7.1966 (2) Å	µ = 0.08 mm⁻¹
c = 12.6520 (3) Å	T = 100 K
β = 106.438 (2)°	Needle, yellow
V = 1715.53 (8) Å³	0.47 × 0.12 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5025 independent reflections
Radiation source: sealed tube	2783 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→27
T_min = 0.962, T_max = 0.997	k = −9→10
20873 measured reflections	l = −17→17

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0907P)²] where P = (F_o² + 2F_c²)/3
5025 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₁H₂₄O₃	V = 1715.53 (8) Å³
M_r = 324.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.6443 (5) Å	µ = 0.08 mm⁻¹
b = 7.1966 (2) Å	T = 100 K
c = 12.6520 (3) Å	0.47 × 0.12 × 0.04 mm
β = 106.438 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5025 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2783 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.997	R_int = 0.057
20873 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	0 restraints
wR(F²) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.53 e Å⁻³
5025 reflections	Δρ_min = −0.29 e Å⁻³
222 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	0.31582 (7)	0.61343 (19)	−0.09249 (11)	0.0210 (3)
O2	0.20488 (6)	0.60487 (18)	−0.03200 (11)	0.0203 (3)
O3	−0.06969 (6)	0.61140 (17)	0.36275 (11)	0.0168 (3)
C1	0.35907 (9)	0.6404 (2)	0.20871 (16)	0.0159 (4)
H1A	0.3371	0.6462	0.2648	0.019*
C2	0.43212 (9)	0.6445 (3)	0.23554 (17)	0.0202 (4)
H2A	0.4590	0.6512	0.3089	0.024*
C3	0.46535 (9)	0.6386 (3)	0.15149 (16)	0.0194 (4)
H3A	0.5146	0.6415	0.1691	0.023*
C4	0.42582 (9)	0.6283 (3)	0.04267 (16)	0.0175 (4)
H4A	0.4485	0.6249	−0.0126	0.021*
C5	0.35182 (9)	0.6230 (2)	0.01518 (15)	0.0149 (4)
C6	0.31698 (9)	0.6276 (2)	0.09933 (15)	0.0137 (4)
C7	0.23827 (9)	0.6181 (2)	0.06736 (15)	0.0138 (4)
C8	0.19935 (9)	0.6221 (2)	0.15096 (16)	0.0146 (4)
H8A	0.2236	0.6250	0.2256	0.018*
C9	0.12783 (9)	0.6216 (2)	0.11734 (16)	0.0153 (4)
H9A	0.1076	0.6215	0.0414	0.018*
C10	0.07792 (8)	0.6213 (2)	0.18274 (15)	0.0130 (4)
C11	0.00511 (9)	0.6329 (2)	0.12710 (16)	0.0154 (4)
H11A	−0.0091	0.6438	0.0507	0.018*
C12	−0.04606 (9)	0.6284 (3)	0.18360 (16)	0.0160 (4)
H12A	−0.0940	0.6344	0.1454	0.019*
C13	−0.02488 (9)	0.6148 (2)	0.29733 (16)	0.0135 (4)
C14	0.04731 (9)	0.6028 (2)	0.35469 (16)	0.0156 (4)
H14A	0.0612	0.5925	0.4311	0.019*
C15	0.09760 (9)	0.6064 (2)	0.29794 (16)	0.0154 (4)
H15A	0.1454	0.5988	0.3366	0.019*
C16	−0.14479 (8)	0.6211 (3)	0.31008 (15)	0.0153 (4)
H16A	−0.1602	0.5148	0.2621	0.018*
H16B	−0.1565	0.7335	0.2664	0.018*
C17	−0.18025 (9)	0.6212 (3)	0.40186 (15)	0.0151 (4)
H17A	−0.1631	0.7269	0.4496	0.018*
H17B	−0.1667	0.5094	0.4455	0.018*
C18	−0.26094 (9)	0.6306 (3)	0.36018 (15)	0.0149 (4)
H18A	−0.2785	0.5255	0.3122	0.018*
H18B	−0.2750	0.7434	0.3176	0.018*
C19	−0.29383 (9)	0.6284 (3)	0.45638 (15)	0.0144 (4)
H19A	−0.2785	0.5166	0.4994	0.017*
H19B	−0.2759	0.7341	0.5037	0.017*
C20	−0.37459 (9)	0.6351 (3)	0.42130 (16)	0.0162 (4)
H20A	−0.3931	0.5290	0.3747	0.019*
H20B	−0.3904	0.7469	0.3786	0.019*
C21	−0.40379 (9)	0.6331 (3)	0.52132 (17)	0.0219 (5)
H21A	−0.4547	0.6385	0.4969	0.033*
H21B	−0.3859	0.7386	0.5672	0.033*
H21C	−0.3892	0.5210	0.5626	0.033*
H1O1	0.2698 (14)	0.605 (3)	−0.094 (2)	0.059 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0199 (7)	0.0333 (9)	0.0108 (7)	−0.0030 (6)	0.0060 (6)	0.0011 (6)
O2	0.0166 (6)	0.0309 (8)	0.0131 (7)	0.0007 (6)	0.0035 (6)	0.0021 (6)
O3	0.0115 (6)	0.0264 (8)	0.0139 (7)	0.0003 (5)	0.0060 (5)	−0.0003 (6)
C1	0.0167 (8)	0.0195 (10)	0.0137 (10)	0.0012 (8)	0.0078 (7)	0.0006 (8)
C2	0.0174 (9)	0.0295 (12)	0.0132 (10)	−0.0017 (8)	0.0035 (8)	0.0002 (9)
C3	0.0142 (8)	0.0238 (11)	0.0213 (11)	−0.0006 (8)	0.0068 (8)	0.0018 (9)
C4	0.0179 (8)	0.0193 (10)	0.0198 (11)	0.0006 (8)	0.0125 (8)	0.0021 (9)
C5	0.0203 (9)	0.0132 (10)	0.0127 (10)	−0.0009 (7)	0.0071 (8)	0.0018 (8)
C6	0.0149 (8)	0.0130 (10)	0.0146 (10)	0.0012 (7)	0.0068 (7)	0.0004 (8)
C7	0.0154 (8)	0.0125 (9)	0.0147 (10)	0.0010 (7)	0.0061 (7)	0.0016 (8)
C8	0.0149 (8)	0.0162 (10)	0.0135 (10)	0.0005 (7)	0.0055 (7)	0.0018 (8)
C9	0.0164 (8)	0.0146 (10)	0.0157 (10)	0.0012 (7)	0.0061 (7)	0.0005 (8)
C10	0.0122 (8)	0.0126 (9)	0.0149 (10)	−0.0001 (7)	0.0049 (7)	−0.0004 (8)
C11	0.0162 (8)	0.0180 (10)	0.0119 (10)	0.0012 (7)	0.0041 (7)	0.0008 (8)
C12	0.0120 (8)	0.0196 (10)	0.0168 (10)	0.0023 (7)	0.0046 (7)	0.0017 (9)
C13	0.0135 (8)	0.0132 (9)	0.0152 (10)	0.0000 (7)	0.0062 (7)	−0.0021 (8)
C14	0.0152 (8)	0.0202 (11)	0.0111 (10)	−0.0004 (7)	0.0031 (7)	0.0007 (8)
C15	0.0115 (8)	0.0173 (10)	0.0170 (10)	−0.0010 (7)	0.0033 (7)	−0.0027 (8)
C16	0.0102 (7)	0.0197 (10)	0.0156 (10)	0.0000 (7)	0.0030 (7)	−0.0002 (8)
C17	0.0145 (8)	0.0177 (10)	0.0142 (10)	0.0016 (7)	0.0061 (7)	0.0004 (8)
C18	0.0148 (8)	0.0167 (10)	0.0153 (10)	−0.0005 (7)	0.0076 (7)	−0.0008 (8)
C19	0.0148 (8)	0.0158 (10)	0.0138 (10)	0.0000 (7)	0.0060 (7)	0.0003 (8)
C20	0.0150 (8)	0.0172 (10)	0.0175 (10)	−0.0002 (7)	0.0065 (7)	0.0011 (8)
C21	0.0176 (9)	0.0283 (12)	0.0231 (12)	0.0018 (8)	0.0112 (8)	0.0040 (10)

Geometric parameters (Å, º) top

O1—C5	1.347 (2)	C12—C13	1.384 (3)
O1—H1O1	0.90 (3)	C12—H12A	0.9300
O2—C7	1.246 (2)	C13—C14	1.401 (2)
O3—C13	1.369 (2)	C14—C15	1.376 (2)
O3—C16	1.438 (2)	C14—H14A	0.9300
C1—C2	1.378 (2)	C15—H15A	0.9300
C1—C6	1.400 (3)	C16—C17	1.514 (2)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.397 (3)	C16—H16B	0.9700
C2—H2A	0.9300	C17—C18	1.524 (2)
C3—C4	1.378 (3)	C17—H17A	0.9700
C3—H3A	0.9300	C17—H17B	0.9700
C4—C5	1.396 (2)	C18—C19	1.531 (2)
C4—H4A	0.9300	C18—H18A	0.9700
C5—C6	1.420 (2)	C18—H18B	0.9700
C6—C7	1.485 (2)	C19—C20	1.522 (2)
C7—C8	1.470 (2)	C19—H19A	0.9700
C8—C9	1.348 (2)	C19—H19B	0.9700
C8—H8A	0.9300	C20—C21	1.530 (3)
C9—C10	1.451 (2)	C20—H20A	0.9700
C9—H9A	0.9300	C20—H20B	0.9700
C10—C15	1.402 (3)	C21—H21A	0.9600
C10—C11	1.406 (2)	C21—H21B	0.9600
C11—C12	1.389 (2)	C21—H21C	0.9600
C11—H11A	0.9300

C5—O1—H1O1	105.5 (18)	C15—C14—H14A	120.0
C13—O3—C16	118.03 (14)	C13—C14—H14A	120.0
C2—C1—C6	121.83 (17)	C14—C15—C10	121.08 (16)
C2—C1—H1A	119.1	C14—C15—H15A	119.5
C6—C1—H1A	119.1	C10—C15—H15A	119.5
C1—C2—C3	119.35 (19)	O3—C16—C17	106.20 (15)
C1—C2—H2A	120.3	O3—C16—H16A	110.5
C3—C2—H2A	120.3	C17—C16—H16A	110.5
C4—C3—C2	120.63 (17)	O3—C16—H16B	110.5
C4—C3—H3A	119.7	C17—C16—H16B	110.5
C2—C3—H3A	119.7	H16A—C16—H16B	108.7
C3—C4—C5	120.20 (17)	C16—C17—C18	113.20 (15)
C3—C4—H4A	119.9	C16—C17—H17A	108.9
C5—C4—H4A	119.9	C18—C17—H17A	108.9
O1—C5—C4	117.70 (16)	C16—C17—H17B	108.9
O1—C5—C6	122.21 (16)	C18—C17—H17B	108.9
C4—C5—C6	120.09 (17)	H17A—C17—H17B	107.8
C1—C6—C5	117.89 (15)	C17—C18—C19	110.86 (15)
C1—C6—C7	123.40 (16)	C17—C18—H18A	109.5
C5—C6—C7	118.71 (17)	C19—C18—H18A	109.5
O2—C7—C8	119.66 (16)	C17—C18—H18B	109.5
O2—C7—C6	119.24 (15)	C19—C18—H18B	109.5
C8—C7—C6	121.09 (17)	H18A—C18—H18B	108.1
C9—C8—C7	118.73 (18)	C20—C19—C18	114.03 (15)
C9—C8—H8A	120.6	C20—C19—H19A	108.7
C7—C8—H8A	120.6	C18—C19—H19A	108.7
C8—C9—C10	129.22 (19)	C20—C19—H19B	108.7
C8—C9—H9A	115.4	C18—C19—H19B	108.7
C10—C9—H9A	115.4	H19A—C19—H19B	107.6
C15—C10—C11	117.84 (15)	C19—C20—C21	111.23 (16)
C15—C10—C9	124.12 (16)	C19—C20—H20A	109.4
C11—C10—C9	118.03 (17)	C21—C20—H20A	109.4
C12—C11—C10	121.51 (17)	C19—C20—H20B	109.4
C12—C11—H11A	119.2	C21—C20—H20B	109.4
C10—C11—H11A	119.2	H20A—C20—H20B	108.0
C13—C12—C11	119.23 (16)	C20—C21—H21A	109.5
C13—C12—H12A	120.4	C20—C21—H21B	109.5
C11—C12—H12A	120.4	H21A—C21—H21B	109.5
O3—C13—C12	125.07 (15)	C20—C21—H21C	109.5
O3—C13—C14	114.56 (16)	H21A—C21—H21C	109.5
C12—C13—C14	120.37 (16)	H21B—C21—H21C	109.5
C15—C14—C13	119.97 (17)

C6—C1—C2—C3	0.9 (3)	C8—C9—C10—C11	175.97 (18)
C1—C2—C3—C4	−0.1 (3)	C15—C10—C11—C12	−0.5 (3)
C2—C3—C4—C5	−0.2 (3)	C9—C10—C11—C12	178.26 (17)
C3—C4—C5—O1	179.86 (18)	C10—C11—C12—C13	0.9 (3)
C3—C4—C5—C6	−0.2 (3)	C16—O3—C13—C12	0.5 (2)
C2—C1—C6—C5	−1.3 (3)	C16—O3—C13—C14	−179.34 (15)
C2—C1—C6—C7	178.43 (16)	C11—C12—C13—O3	179.13 (17)
O1—C5—C6—C1	−179.10 (17)	C11—C12—C13—C14	−1.0 (3)
C4—C5—C6—C1	1.0 (3)	O3—C13—C14—C15	−179.48 (16)
O1—C5—C6—C7	1.1 (3)	C12—C13—C14—C15	0.6 (3)
C4—C5—C6—C7	−178.82 (16)	C13—C14—C15—C10	−0.2 (3)
C1—C6—C7—O2	−179.21 (18)	C11—C10—C15—C14	0.1 (3)
C5—C6—C7—O2	0.6 (3)	C9—C10—C15—C14	−178.55 (17)
C1—C6—C7—C8	0.2 (3)	C13—O3—C16—C17	−178.12 (14)
C5—C6—C7—C8	179.95 (16)	O3—C16—C17—C18	−179.87 (14)
O2—C7—C8—C9	−3.6 (3)	C16—C17—C18—C19	179.43 (15)
C6—C7—C8—C9	177.02 (16)	C17—C18—C19—C20	−179.30 (15)
C7—C8—C9—C10	178.62 (18)	C18—C19—C20—C21	−179.83 (15)
C8—C9—C10—C15	−5.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.90 (3)	1.68 (3)	2.507 (2)	152 (2)
C20—H20A···Cg1ⁱ	0.97	2.84	3.657 (2)	142
C20—H20B···Cg1ⁱⁱ	0.97	2.78	3.637 (2)	147

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄O₃
M_r	324.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	19.6443 (5), 7.1966 (2), 12.6520 (3)
β (°)	106.438 (2)
V (Å³)	1715.53 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.47 × 0.12 × 0.04

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.962, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	20873, 5025, 2783
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.190, 1.05
No. of reflections	5025
No. of parameters	222
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.29

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	0.90 (3)	1.68 (3)	2.507 (2)	152 (2)
C20—H20A···Cg1ⁱ	0.97	2.84	3.657 (2)	142
C20—H20B···Cg1ⁱⁱ	0.97	2.78	3.637 (2)	147

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, 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 the Science Fund grant No. 305/PFIZIK/613312 and for the Research University Golden Goose grant No.1001/PFIZIK/811012. ZN and HH thank Universiti Malaysia Sarawak for the Geran Penyelidikan Dana Khas Inovasi, grant No. DI/01/2007(01). SMHF thanks the Malaysian Government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett. 15, 3177–3180. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Lee, Y. S., Lim, S. S., Shin, K. H., Kim, Y. S., Ohuchi, K. & Jung, S. H. (2006). Biol. Pharm. Bull. 29, 1028–1031. Web of Science CrossRef PubMed CAS Google Scholar
Ngaini, Z., Fadzillah, S. M. H., Rahman, N. I. A., Hussain, H., Razak, I. A. & Fun, H.-K. (2009). Acta Cryst. E65, o879–o880. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ngaini, Z., Rahman, N. I. A., Hussain, H., Razak, I. A. & Fun, H.-K. (2009). Acta Cryst. E65, o889–o890. Web of Science CSD CrossRef IUCr Journals Google Scholar
Razak, I. A., Fun, H.-K., Ngaini, Z., Fadzillah, S. M. H. & Hussain, H. (2009a). Acta Cryst. E65, o881–o882. Web of Science CSD CrossRef IUCr Journals Google Scholar
Razak, I. A., Fun, H.-K., Ngaini, Z., Fadzillah, S. M. H. & Hussain, H. (2009b). Acta Cryst. E65, o1133–o1134. Web of Science CSD CrossRef IUCr Journals Google Scholar
Razak, I. A., Fun, H.-K., Ngaini, Z., Rahman, N. I. A. & Hussain, H. (2009). Acta Cryst. E65, o1092–o1093. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xue, C. X., Cui, S. Y., Liu, M. C., Hu, Z. D. & Fan, B. T. (2004). Eur. J. Med. Chem. 39, 745–753. Web of Science CrossRef PubMed CAS Google Scholar
Zhao, L. M., Jin, H. S., Sun, L. P., Piao, H. R. & Quan, Z. S. (2005). Chem. Lett. 15, 5027–5029. CrossRef CAS Google Scholar