(E)-3-[4-(Hex­yloxy)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/S1600536809019436

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages o1439-o1440

doi:10.1107/S1600536809019436

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(E)-3-[4-(Hexyloxy)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 19 May 2009; accepted 22 May 2009; online 29 May 2009)

In the title compound, C₂₁H₂₄O₃, the enone group adopts an s–cis conformation. The planes of the aromatic rings are inclined at an angle of 6.1 (1)°. The alkoxy tail is not linear, with the maximum deviation from the least-squares plane being 0.375 (2) Å. Molecules are connected into extended chains along the a axis through O—H⋯O_carbonyl hydrogen bonds and are interlinked via C—H⋯O interactions to form a two-dimensional array parallel to the ab plane.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ); Xue et al. (2004 ); Zhao et al. (2005 ); Satyanarayana et al. (2004 ); Won et al. (2005 ). For related structures, see: Razak et al. (2009 ); Razak et al. (2009a ,b ); Ngaini, Fadzillah et al. (2009 ); Ngaini, Rahman et al. (2009 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₂₄O₃
M_r = 324.40
Orthorhombic, P b c a
a = 10.0237 (2) Å
b = 9.7695 (2) Å
c = 35.3220 (6) Å
V = 3458.96 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.12 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.980, T_max = 0.995
25370 measured reflections
5659 independent reflections
3311 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.139
S = 1.02
5659 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2ⁱ	0.89 (3)	1.77 (3)	2.6466 (19)	169 (2)
C1—H1A⋯O1ⁱⁱ	0.93	2.55	3.458 (2)	164
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536809019436/tk2457sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019436/tk2457Isup2.hkl

checkCIF report

Comment top

Chalcones derivatives are reported to demonstrate biological properties such as an anti-malarial (Xue et al., 2004), anti-cancer (Bhat et al., 2005), anti-inflammatory (Won et al., 2005), anti-platelet (Zhao et al., 2005) as well as anti-hyperglycemic (Satyanarayana et al., 2004) activities. Synthetic and naturally occurring chalcones have been extensively studied and developed as pharmaceutically important molecules. As part of our studies, we have synthesized the title chalcone derivative, (I), and tested its anti-bacterial activity against E. coli ATCC 8739; the compound showed anti-microbial activity. In this paper, we report the crystal structure of (I).

The conformation of the enone (O2/C7–C9) moiety in (I) is s–cis with the O2—C7—C8—C9 torsion angle being 5.7 (3)°. The mean plane through the enone moiety makes dihedral angles of 15.9 (1)° and 10.9 (1)°, with the C1–C6 and C10–C15 aromatic rings, respectively. The two aromatic rings form a dihedral angle of 6.1 (1)°.

The short H1A···H8A (2.16 Å) contact resulted in the slight widening of the C1—C6—C7 (123.0 (2)°) and C6—C7—C8 (120.7 (2)°) angles whereas the widening of C8—C9—C10 and C9—C10—C15 angles to 129.0 (2)° and 123.7 (2)° respectively, resulted from the close interatomic contact of H8A···H15A (2.34 Å). Correspondingly, the opening of the O3—C13—C12 (124.9 (2)°) angle is the consequence of strain induced by short H12A···H16A (2.28 Å) and H12A···H16B (2.38 Å) contacts. Similar features can also be found in previously reported related structures (Razak et al., 2009; Razak et al., 2009a,b; Ngaini, Fadzillah et al., 2009; Ngaini, Rahman et al., 2009).

Even though the C16—O3—C13—C12 torsion angle is 0.8 (3)°, only part of the alkoxyl tail, O3/C16–C18, is co-planar with the attached aromatic ring [maximum deviation of the least-squares plane of O3/C16–C18 is -0.002 (2) Å]. The alkoxyl chain is twisted about the C19—C20 bond as shown by the C18—C19—C20—C21 torsion angle being -73.4 (2)°. The least-squares plane through the the alkoxyl chain, O3/C16–C21, [maximum deviation of 0.375 (2) Å at C16] makes a dihedral angle of 49.1 (2)° with the attached aromatic ring.

In the crystal structure, intermolecular O1—H1O1···O2 hydrogen bonds between the hydroxy and keto groups link the molecules into extended chains along the a axis, Table 1. The chains are interlinked via C1—H1A···O1 interactions into a 2-D array parallel to the ab-plane, Table 1 and Fig. 2.

Related literature top

For the biological properties of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004); Zhao et al. (2005); Satyanarayana et al. (2004); Won et al. (2005). For related structures, see: Razak et al. (2009); Razak et al. (2009a,b); Ngaini, Fadzillah et al. (2009); Ngaini, Rahman et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 4-hydroxyacetophenone (1.36 g, 10 mmol), 4-hexyloxybenzaldehyde (2.06 ml, 10 mmol) and KOH (2.02 g, 36 mmol) in methanol (30 ml) was heated at reflux for 24 h. The reaction 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 (I), showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing in (I), viewed down the a axis. Intermolecular O—H···O hydrogen bonding and C—H···O contacts are shown as dashed lines. H atoms not involved in hydrogen bondings are omitted for clarity.

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

Crystal data top

C₂₁H₂₄O₃	F(000) = 1392
M_r = 324.40	D_x = 1.246 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2200 reflections
a = 10.0237 (2) Å	θ = 2.3–22.0°
b = 9.7695 (2) Å	µ = 0.08 mm⁻¹
c = 35.3220 (6) Å	T = 100 K
V = 3458.96 (12) Å³	Block, colourless
Z = 8	0.25 × 0.12 × 0.07 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5659 independent reflections
Radiation source: sealed tube	3311 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ϕ and ω scans	θ_max = 31.3°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
T_min = 0.980, T_max = 0.995	k = −14→14
25370 measured reflections	l = −51→50

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0389P)² + 1.4637P] where P = (F_o² + 2F_c²)/3
5659 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₁H₂₄O₃	V = 3458.96 (12) Å³
M_r = 324.40	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.0237 (2) Å	µ = 0.08 mm⁻¹
b = 9.7695 (2) Å	T = 100 K
c = 35.3220 (6) Å	0.25 × 0.12 × 0.07 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5659 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3311 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.995	R_int = 0.086
25370 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.27 e Å⁻³
5659 reflections	Δρ_min = −0.25 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	0.45711 (14)	0.93154 (14)	0.31262 (3)	0.0203 (3)
O2	0.17214 (13)	0.81942 (14)	0.15690 (3)	0.0216 (3)
O3	0.47446 (13)	0.24927 (13)	0.00413 (4)	0.0207 (3)
C1	0.43756 (18)	0.74282 (19)	0.22313 (5)	0.0177 (4)
H1A	0.4783	0.6696	0.2109	0.021*
C2	0.47890 (19)	0.77884 (18)	0.25929 (5)	0.0183 (4)
H2A	0.5452	0.7286	0.2714	0.022*
C3	0.42085 (18)	0.89013 (19)	0.27736 (5)	0.0172 (4)
C4	0.32103 (19)	0.96503 (19)	0.25923 (5)	0.0198 (4)
H4A	0.2827	1.0402	0.2712	0.024*
C5	0.27945 (18)	0.92715 (19)	0.22348 (5)	0.0193 (4)
H5A	0.2127	0.9773	0.2116	0.023*
C6	0.33582 (18)	0.81466 (18)	0.20480 (5)	0.0163 (4)
C7	0.28184 (18)	0.77389 (19)	0.16745 (5)	0.0175 (4)
C8	0.35542 (18)	0.67861 (19)	0.14301 (5)	0.0177 (4)
H8A	0.4336	0.6379	0.1516	0.021*
C9	0.30968 (18)	0.65064 (19)	0.10828 (5)	0.0184 (4)
H9A	0.2357	0.7010	0.1007	0.022*
C10	0.35965 (18)	0.55225 (18)	0.08071 (5)	0.0169 (4)
C11	0.29114 (19)	0.5369 (2)	0.04661 (5)	0.0201 (4)
H11A	0.2197	0.5948	0.0415	0.024*
C12	0.32554 (19)	0.43872 (19)	0.02008 (5)	0.0201 (4)
H12A	0.2773	0.4303	−0.0023	0.024*
C13	0.43319 (18)	0.35286 (18)	0.02730 (5)	0.0176 (4)
C14	0.50604 (18)	0.3682 (2)	0.06095 (5)	0.0193 (4)
H14A	0.5795	0.3125	0.0655	0.023*
C15	0.46928 (18)	0.46577 (19)	0.08730 (5)	0.0180 (4)
H15A	0.5176	0.4743	0.1096	0.022*
C16	0.40164 (19)	0.2288 (2)	−0.03062 (5)	0.0207 (4)
H16A	0.4010	0.3125	−0.0454	0.025*
H16B	0.3101	0.2034	−0.0251	0.025*
C17	0.47013 (19)	0.11601 (19)	−0.05233 (5)	0.0211 (4)
H17A	0.4708	0.0334	−0.0371	0.025*
H17B	0.5620	0.1420	−0.0571	0.025*
C18	0.4013 (2)	0.0863 (2)	−0.08992 (5)	0.0229 (4)
H18A	0.3874	0.1717	−0.1033	0.027*
H18B	0.3145	0.0462	−0.0850	0.027*
C19	0.48161 (19)	−0.0107 (2)	−0.11501 (5)	0.0219 (4)
H19A	0.4997	−0.0939	−0.1009	0.026*
H19B	0.5667	0.0318	−0.1208	0.026*
C20	0.4129 (2)	−0.0490 (2)	−0.15221 (5)	0.0274 (5)
H20A	0.3798	0.0336	−0.1642	0.033*
H20B	0.4781	−0.0899	−0.1691	0.033*
C21	0.2977 (2)	−0.1482 (2)	−0.14688 (6)	0.0286 (5)
H21A	0.2614	−0.1722	−0.1711	0.043*
H21B	0.2297	−0.1057	−0.1317	0.043*
H21C	0.3291	−0.2292	−0.1344	0.043*
H1O1	0.529 (3)	0.886 (3)	0.3205 (7)	0.057 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0221 (7)	0.0227 (7)	0.0162 (6)	0.0010 (6)	−0.0029 (6)	−0.0022 (6)
O2	0.0217 (7)	0.0263 (7)	0.0169 (6)	0.0043 (6)	−0.0023 (5)	−0.0003 (6)
O3	0.0243 (7)	0.0219 (7)	0.0160 (6)	0.0026 (6)	−0.0010 (5)	−0.0046 (5)
C1	0.0195 (9)	0.0155 (9)	0.0182 (9)	−0.0003 (8)	0.0009 (8)	−0.0010 (7)
C2	0.0206 (10)	0.0158 (9)	0.0184 (9)	0.0010 (8)	−0.0036 (8)	0.0011 (7)
C3	0.0191 (9)	0.0193 (9)	0.0132 (8)	−0.0041 (7)	−0.0003 (7)	0.0001 (7)
C4	0.0196 (9)	0.0177 (9)	0.0221 (9)	0.0013 (8)	0.0019 (8)	−0.0025 (8)
C5	0.0192 (9)	0.0193 (9)	0.0194 (9)	0.0008 (8)	−0.0023 (7)	−0.0002 (8)
C6	0.0179 (9)	0.0163 (8)	0.0148 (8)	−0.0011 (7)	0.0003 (7)	0.0014 (7)
C7	0.0199 (9)	0.0173 (9)	0.0153 (9)	−0.0027 (8)	0.0010 (7)	0.0023 (7)
C8	0.0172 (9)	0.0183 (9)	0.0175 (9)	0.0012 (8)	0.0004 (7)	0.0023 (7)
C9	0.0179 (9)	0.0194 (9)	0.0178 (9)	−0.0005 (7)	0.0020 (7)	0.0020 (8)
C10	0.0189 (9)	0.0177 (9)	0.0141 (8)	−0.0026 (7)	0.0012 (7)	0.0015 (7)
C11	0.0201 (10)	0.0217 (10)	0.0184 (9)	0.0016 (8)	−0.0006 (8)	0.0025 (8)
C12	0.0228 (10)	0.0239 (10)	0.0135 (8)	−0.0005 (8)	−0.0026 (8)	−0.0007 (8)
C13	0.0211 (9)	0.0161 (9)	0.0155 (9)	−0.0023 (7)	0.0032 (7)	0.0018 (7)
C14	0.0167 (9)	0.0218 (9)	0.0195 (9)	0.0001 (8)	0.0001 (7)	0.0021 (8)
C15	0.0198 (9)	0.0214 (9)	0.0128 (8)	−0.0032 (8)	0.0001 (7)	0.0017 (7)
C16	0.0235 (10)	0.0228 (10)	0.0157 (9)	−0.0004 (8)	−0.0013 (8)	0.0010 (8)
C17	0.0238 (10)	0.0208 (9)	0.0188 (9)	0.0022 (8)	0.0017 (8)	−0.0009 (8)
C18	0.0270 (11)	0.0223 (10)	0.0194 (9)	0.0038 (8)	0.0010 (8)	−0.0017 (8)
C19	0.0253 (10)	0.0203 (9)	0.0201 (9)	−0.0005 (8)	0.0050 (8)	−0.0014 (8)
C20	0.0399 (13)	0.0245 (10)	0.0178 (10)	−0.0012 (10)	0.0031 (9)	−0.0018 (8)
C21	0.0344 (12)	0.0286 (11)	0.0228 (10)	0.0021 (10)	−0.0038 (9)	−0.0021 (9)

Geometric parameters (Å, º) top

O1—C3	1.359 (2)	C12—C13	1.390 (3)
O1—H1O1	0.89 (3)	C12—H12A	0.9300
O2—C7	1.243 (2)	C13—C14	1.403 (2)
O3—C13	1.366 (2)	C14—C15	1.382 (3)
O3—C16	1.442 (2)	C14—H14A	0.9300
C1—C2	1.388 (2)	C15—H15A	0.9300
C1—C6	1.397 (2)	C16—C17	1.508 (3)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.389 (2)	C16—H16B	0.9700
C2—H2A	0.9300	C17—C18	1.524 (3)
C3—C4	1.395 (3)	C17—H17A	0.9700
C4—C5	1.380 (2)	C17—H17B	0.9700
C4—H4A	0.9300	C18—C19	1.526 (3)
C5—C6	1.401 (2)	C18—H18A	0.9700
C5—H5A	0.9300	C18—H18B	0.9700
C6—C7	1.481 (2)	C19—C20	1.530 (3)
C7—C8	1.468 (3)	C19—H19A	0.9700
C8—C9	1.338 (2)	C19—H19B	0.9700
C8—H8A	0.9300	C20—C21	1.519 (3)
C9—C10	1.457 (2)	C20—H20A	0.9700
C9—H9A	0.9300	C20—H20B	0.9700
C10—C11	1.394 (2)	C21—H21A	0.9600
C10—C15	1.405 (3)	C21—H21B	0.9600
C11—C12	1.385 (3)	C21—H21C	0.9600
C11—H11A	0.9300

C3—O1—H1O1	110.8 (17)	C15—C14—H14A	119.8
C13—O3—C16	117.35 (14)	C13—C14—H14A	119.8
C2—C1—C6	121.13 (17)	C14—C15—C10	120.75 (17)
C2—C1—H1A	119.4	C14—C15—H15A	119.6
C6—C1—H1A	119.4	C10—C15—H15A	119.6
C1—C2—C3	119.76 (17)	O3—C16—C17	107.68 (15)
C1—C2—H2A	120.1	O3—C16—H16A	110.2
C3—C2—H2A	120.1	C17—C16—H16A	110.2
O1—C3—C2	122.84 (16)	O3—C16—H16B	110.2
O1—C3—C4	117.15 (16)	C17—C16—H16B	110.2
C2—C3—C4	120.01 (16)	H16A—C16—H16B	108.5
C5—C4—C3	119.72 (17)	C16—C17—C18	112.12 (16)
C5—C4—H4A	120.1	C16—C17—H17A	109.2
C3—C4—H4A	120.1	C18—C17—H17A	109.2
C4—C5—C6	121.30 (17)	C16—C17—H17B	109.2
C4—C5—H5A	119.4	C18—C17—H17B	109.2
C6—C5—H5A	119.4	H17A—C17—H17B	107.9
C1—C6—C5	118.05 (16)	C17—C18—C19	112.69 (16)
C1—C6—C7	123.00 (16)	C17—C18—H18A	109.1
C5—C6—C7	118.90 (16)	C19—C18—H18A	109.1
O2—C7—C8	119.66 (16)	C17—C18—H18B	109.1
O2—C7—C6	119.61 (16)	C19—C18—H18B	109.1
C8—C7—C6	120.73 (16)	H18A—C18—H18B	107.8
C9—C8—C7	119.77 (17)	C18—C19—C20	114.40 (17)
C9—C8—H8A	120.1	C18—C19—H19A	108.7
C7—C8—H8A	120.1	C20—C19—H19A	108.7
C8—C9—C10	129.03 (18)	C18—C19—H19B	108.7
C8—C9—H9A	115.5	C20—C19—H19B	108.7
C10—C9—H9A	115.5	H19A—C19—H19B	107.6
C11—C10—C15	117.62 (17)	C21—C20—C19	113.07 (16)
C11—C10—C9	118.60 (17)	C21—C20—H20A	109.0
C15—C10—C9	123.68 (16)	C19—C20—H20A	109.0
C12—C11—C10	122.42 (18)	C21—C20—H20B	109.0
C12—C11—H11A	118.8	C19—C20—H20B	109.0
C10—C11—H11A	118.8	H20A—C20—H20B	107.8
C11—C12—C13	119.14 (17)	C20—C21—H21A	109.5
C11—C12—H12A	120.4	C20—C21—H21B	109.5
C13—C12—H12A	120.4	H21A—C21—H21B	109.5
O3—C13—C12	124.91 (16)	C20—C21—H21C	109.5
O3—C13—C14	115.42 (16)	H21A—C21—H21C	109.5
C12—C13—C14	119.66 (17)	H21B—C21—H21C	109.5
C15—C14—C13	120.37 (18)

C6—C1—C2—C3	−1.6 (3)	C8—C9—C10—C15	0.9 (3)
C1—C2—C3—O1	−179.56 (16)	C15—C10—C11—C12	1.6 (3)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—C12	−174.97 (17)
O1—C3—C4—C5	−179.55 (16)	C10—C11—C12—C13	−0.8 (3)
C2—C3—C4—C5	0.7 (3)	C16—O3—C13—C12	0.8 (3)
C3—C4—C5—C6	−0.2 (3)	C16—O3—C13—C14	179.42 (15)
C2—C1—C6—C5	2.0 (3)	C11—C12—C13—O3	177.71 (17)
C2—C1—C6—C7	−175.46 (17)	C11—C12—C13—C14	−0.9 (3)
C4—C5—C6—C1	−1.1 (3)	O3—C13—C14—C15	−177.06 (16)
C4—C5—C6—C7	176.46 (17)	C12—C13—C14—C15	1.7 (3)
C1—C6—C7—O2	162.42 (17)	C13—C14—C15—C10	−0.8 (3)
C5—C6—C7—O2	−15.0 (3)	C11—C10—C15—C14	−0.8 (3)
C1—C6—C7—C8	−16.6 (3)	C9—C10—C15—C14	175.58 (17)
C5—C6—C7—C8	165.93 (16)	C13—O3—C16—C17	176.52 (15)
O2—C7—C8—C9	5.7 (3)	O3—C16—C17—C18	−179.69 (15)
C6—C7—C8—C9	−175.26 (17)	C16—C17—C18—C19	170.71 (16)
C7—C8—C9—C10	−174.51 (17)	C17—C18—C19—C20	177.08 (17)
C8—C9—C10—C11	177.22 (19)	C18—C19—C20—C21	−73.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	0.89 (3)	1.77 (3)	2.6466 (19)	169 (2)
C1—H1A···O1ⁱⁱ	0.93	2.55	3.458 (2)	164

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄O₃
M_r	324.40
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	10.0237 (2), 9.7695 (2), 35.3220 (6)
V (Å³)	3458.96 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.12 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.980, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	25370, 5659, 3311
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.731

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.139, 1.02
No. of reflections	5659
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)	0.27, −0.25

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	0.89 (3)	1.77 (3)	2.6466 (19)	169 (2)
C1—H1A···O1ⁱⁱ	0.93	2.55	3.458 (2)	164

Symmetry codes: (i) x+1/2, y, −z+1/2; (ii) −x+1, 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 a Science Fund grant (No. 305/PFIZIK/613312) and a Research University Golden Goose grant (No. 1001/PFIZIK/811012). ZN and HH thank Universiti Malaysia Sarawak for a 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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