(E)-1-(3-Hy­droxy­phen­yl)-3-[4-(tetra­dec­yl­oxy)phen­yl]prop-2-en-1-one

Fadzillah, S.M.H.; Ngaini, Z.; Hussain, H.; Razak, I.A.; Asik, S.I.J.

doi:10.1107/S1600536812038020

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 10| October 2012| Pages o2911-o2912

https://doi.org/10.1107/S1600536812038020

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(E)-1-(3-Hydroxyphenyl)-3-[4-(tetradecyloxy)phenyl]prop-2-en-1-one

Siti Muhaini Haris Fadzillah,^a Zainab Ngaini,^a Hasnain Hussain,^b Ibrahim Abdul Razak ^c ^*‡ and Safra Izuani Jama Asik ^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 ^cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 29 August 2012; accepted 4 September 2012; online 8 September 2012)

In the title compound, C₂₉H₄₀O₃, the enone moiety adopts an s-cis conformation. The dihedral angle between the benzene rings is 4.33 (5)° The least-squares mean line through the tetradecyl side chain forms a dihedral angle of 83.99 (7)° with the normal to the attached benzene ring. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds involving the keto and the hydroxy O atoms form ribbons along [-41-1]. The crystal structure also features C—H⋯π interactions.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ); Xue et al. (2004 ); Won et al. (2005 ); Zhao et al. (2005 ); Satyanarayana et al. (2004 ). For related structures, see: Razak et al. (2009 ); Ngaini et al. (2010 , 2011 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₉H₄₀O₃
M_r = 436.61
Triclinic, $[P \overline 1]$
a = 6.5138 (16) Å
b = 10.155 (2) Å
c = 19.264 (5) Å
α = 75.361 (6)°
β = 85.872 (7)°
γ = 83.013 (6)°
V = 1222.6 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.29 × 0.12 × 0.08 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.979, T_max = 0.994
26295 measured reflections
7155 independent reflections
5052 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.147
S = 0.95
7155 reflections
293 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2ⁱ	0.93 (2)	1.80 (2)	2.7269 (14)	175.6 (18)
C29—H29A⋯O1ⁱⁱ	0.96	2.44	3.3589 (18)	160
C17—H17B⋯Cg1ⁱⁱⁱ	0.97	2.73	3.6159 (16)	152
C28—H28A⋯Cg2^iv	0.97	2.93	3.8481 (16)	159
Symmetry codes: (i) -x+3, -y, -z+1; (ii) x-4, y+1, z-1; (iii) x-1, y, z; (iv) x-3, y+1, z-1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812038020/rz5001sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038020/rz5001Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038020/rz5001Isup3.cml

checkCIF report

Comment top

Chalcones are highly reactive subtances of varied nature. They have been reported to possess many useful properties including anti-malarial (Xue et al., 2004), anti-cancer (Bhat et al., 2005), anti-inflammatory (Won et al., 2005), anti-platelet (Zhao et al., 2005) and anti-hyperglynemic (Satyanarayana et al., 2004) activities. Herein, we report the crystal structure of the title compound (Fig. 1).

The enone moiety (O2/C7–C9) adopts an s-cis conformation with the O2–C7–C8–C9 torsion angle of 0.64 (17)°. The dihedral angles between the least-square plane through the enone moiety and the benzene rings (C1–C6 and C10–C15) are 6.26 (7) and 4.65 (7)°, respectively. The dihedral angle between these benzene rings is 4.33 (5)°. The bond lengths observed in the title compound are comparable with the values previously reported values in the literature (Allen et al., 1987).

The short H8A···H15A (2.20 Å) and H8A···H1A (2.11 Å) contacts results in the widening of C8–C9–C10 (126.84 (11)°) and C1–C6–C7 (123.31 (10)°) angles, respectively. The geometric parameters are consistent to those observed in closely related structures (Razak et al., 2009; Ngaini et al., 2010; Ngaini et al., 2011).

The conformation throughout the zigzag alkoxyl tail is trans and is roughly coplanar with the attached benzene (C10–C15) ring as the torsion angle C16–O3–C13–C14 is 176.57 (10)°. However, only the aliphatic part (C16–C29) of the alkoxyl tail is constantly within the zigzag plane. The torsion angle of the aliphatic part deviate from the ideal value by 0.02 (10)–3.75 (10)° while the O3–C16–C17–C18 torsion angle shows value of 173.64 (9)°.

In the crystal packing (Fig. 2), the molecules are arranged in head-to-tail manner along the [-4 1 -1] direction. This arrangement is linked into extended chains through C29—H29···O1 intermolecular interactions. These chains are alternately interconnected by O1—H1O1···O2 intermolecuar hydrogen bonds. Furthermore, the crystal packing is stabilized by weak C—H···π interactions (Table 1) with the distance of 3.6159 (16) and 3.8481 (16) Å.

Related literature top

For the biological properties of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004); Won et al. (2005); Zhao et al. (2005); Satyanarayana et al. (2004). For related structures, see: Razak et al. (2009); Ngaini et al. (2010, 2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 3-hydroxyacetophenone (1.36 g, 10 mmol) and 4-tetradecyloxybenzaldehyde (3.19 ml, 10 mmol) in methanol (40 ml) was heated at reflux for 12 h. The reaction was cooled to room temperature and acidified with cold diluted HCl (2N). The resulting precipitate was filtered, washed and dried. After redissolving in hexane-ethanol (7:1 v/v) followed by few days of slow evaporation, crystals were collected.

Structure description top

For the biological properties of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004); Won et al. (2005); Zhao et al. (2005); Satyanarayana et al. (2004). For related structures, see: Razak et al. (2009); Ngaini et al. (2010, 2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound viewed down the a axis, showing the alternately interconnected extended chains parallel to the [4 -1 1] direction. Hydrogen atoms not involved in hydrogen bonds (dashed lines) are omitted.

(E)-1-(3-Hydroxyphenyl)-3-[4-(tetradecyloxy)phenyl]prop-2-en-1-one top

Crystal data top

C₂₉H₄₀O₃	Z = 2
M_r = 436.61	F(000) = 476
Triclinic, P1	D_x = 1.186 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5138 (16) Å	Cell parameters from 5533 reflections
b = 10.155 (2) Å	θ = 2.6–30.1°
c = 19.264 (5) Å	µ = 0.08 mm⁻¹
α = 75.361 (6)°	T = 100 K
β = 85.872 (7)°	Block, colourless
γ = 83.013 (6)°	0.29 × 0.12 × 0.08 mm
V = 1222.6 (5) Å³

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7155 independent reflections
Radiation source: fine-focus sealed tube	5052 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 30.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.979, T_max = 0.994	k = −14→14
26295 measured reflections	l = −27→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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0913P)² + 0.1348P] where P = (F_o² + 2F_c²)/3
7155 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₉H₄₀O₃	γ = 83.013 (6)°
M_r = 436.61	V = 1222.6 (5) Å³
Triclinic, P1	Z = 2
a = 6.5138 (16) Å	Mo Kα radiation
b = 10.155 (2) Å	µ = 0.08 mm⁻¹
c = 19.264 (5) Å	T = 100 K
α = 75.361 (6)°	0.29 × 0.12 × 0.08 mm
β = 85.872 (7)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	7155 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5052 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.994	R_int = 0.037
26295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.40 e Å⁻³
7155 reflections	Δρ_min = −0.23 e Å⁻³
293 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 > 2sigma(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	1.67428 (14)	0.11123 (9)	0.62770 (5)	0.0245 (2)
O2	1.18019 (13)	0.07397 (8)	0.44966 (4)	0.01891 (19)
O3	0.03940 (13)	0.44359 (8)	0.27772 (4)	0.01874 (19)
C1	1.10873 (19)	0.31949 (12)	0.55966 (6)	0.0187 (2)
H1A	0.9815	0.3669	0.5452	0.022*
C2	1.2188 (2)	0.35854 (12)	0.60903 (6)	0.0210 (3)
H2A	1.1648	0.4326	0.6273	0.025*
C3	1.4073 (2)	0.28868 (12)	0.63122 (6)	0.0193 (2)
H3A	1.4798	0.3158	0.6642	0.023*
C4	1.48910 (19)	0.17725 (11)	0.60411 (6)	0.0168 (2)
C5	1.37933 (18)	0.13808 (11)	0.55490 (6)	0.0159 (2)
H5A	1.4331	0.0635	0.5370	0.019*
C6	1.19002 (18)	0.20879 (11)	0.53191 (5)	0.0147 (2)
C7	1.08792 (18)	0.16453 (11)	0.47562 (5)	0.0149 (2)
C8	0.88422 (19)	0.23100 (11)	0.45154 (6)	0.0175 (2)
H8A	0.8178	0.2985	0.4726	0.021*
C9	0.79155 (18)	0.19653 (11)	0.39981 (6)	0.0157 (2)
H9A	0.8609	0.1263	0.3814	0.019*
C10	0.59375 (18)	0.25740 (11)	0.36941 (5)	0.0148 (2)
C11	0.51656 (19)	0.20878 (11)	0.31596 (6)	0.0165 (2)
H11A	0.5911	0.1353	0.3017	0.020*
C12	0.33214 (19)	0.26639 (11)	0.28337 (6)	0.0162 (2)
H12A	0.2838	0.2318	0.2480	0.019*
C13	0.22125 (18)	0.37651 (11)	0.30454 (5)	0.0151 (2)
C14	0.29544 (19)	0.42667 (11)	0.35819 (6)	0.0167 (2)
H14A	0.2211	0.5005	0.3722	0.020*
C15	0.47706 (18)	0.36780 (11)	0.39023 (6)	0.0163 (2)
H15A	0.5235	0.4015	0.4262	0.020*
C16	−0.04781 (19)	0.40731 (11)	0.21970 (6)	0.0169 (2)
H16A	−0.0784	0.3128	0.2336	0.020*
H16B	0.0467	0.4194	0.1779	0.020*
C17	−0.24440 (19)	0.50374 (11)	0.20419 (6)	0.0166 (2)
H17A	−0.2112	0.5967	0.1981	0.020*
H17B	−0.3398	0.4836	0.2456	0.020*
C18	−0.35328 (18)	0.49674 (11)	0.13800 (6)	0.0166 (2)
H18A	−0.3893	0.4046	0.1436	0.020*
H18B	−0.2605	0.5182	0.0960	0.020*
C19	−0.54867 (18)	0.59744 (11)	0.12739 (6)	0.0167 (2)
H19A	−0.6427	0.5718	0.1687	0.020*
H19B	−0.5117	0.6878	0.1259	0.020*
C20	−0.66224 (19)	0.60539 (11)	0.05978 (6)	0.0171 (2)
H20A	−0.5696	0.6318	0.0181	0.021*
H20B	−0.7009	0.5155	0.0610	0.021*
C21	−0.85585 (18)	0.70750 (11)	0.05220 (6)	0.0169 (2)
H21A	−0.8168	0.7965	0.0525	0.020*
H21B	−0.9489	0.6796	0.0936	0.020*
C22	−0.97131 (19)	0.72124 (11)	−0.01577 (6)	0.0169 (2)
H22A	−0.8797	0.7513	−0.0573	0.020*
H22B	−1.0086	0.6321	−0.0167	0.020*
C23	−1.16618 (18)	0.82165 (11)	−0.02125 (6)	0.0174 (2)
H23A	−1.2582	0.7907	0.0200	0.021*
H23B	−1.1288	0.9103	−0.0195	0.021*
C24	−1.28162 (19)	0.83808 (11)	−0.08925 (6)	0.0175 (2)
H24A	−1.3187	0.7494	−0.0912	0.021*
H24B	−1.1901	0.8696	−0.1306	0.021*
C25	−1.47682 (19)	0.93813 (11)	−0.09405 (6)	0.0178 (2)
H25A	−1.4395	1.0267	−0.0921	0.021*
H25B	−1.5681	0.9066	−0.0526	0.021*
C26	−1.59373 (19)	0.95536 (11)	−0.16197 (6)	0.0173 (2)
H26A	−1.5028	0.9869	−0.2035	0.021*
H26B	−1.6319	0.8670	−0.1639	0.021*
C27	−1.78807 (19)	1.05606 (12)	−0.16597 (6)	0.0189 (2)
H27A	−1.7484	1.1453	−0.1665	0.023*
H27B	−1.8745	1.0272	−0.1229	0.023*
C28	−1.9153 (2)	1.06977 (12)	−0.23116 (6)	0.0193 (2)
H28A	−1.8286	1.0958	−0.2744	0.023*
H28B	−1.9611	0.9817	−0.2298	0.023*
C29	−2.1028 (2)	1.17540 (13)	−0.23412 (7)	0.0252 (3)
H29A	−2.1781	1.1808	−0.2760	0.038*
H29B	−2.0581	1.2631	−0.2364	0.038*
H29C	−2.1907	1.1490	−0.1919	0.038*
H1O1	1.718 (3)	0.046 (2)	0.6024 (10)	0.056 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0180 (5)	0.0297 (5)	0.0300 (4)	0.0089 (4)	−0.0123 (4)	−0.0174 (4)
O2	0.0174 (5)	0.0197 (4)	0.0206 (4)	0.0027 (3)	−0.0034 (3)	−0.0084 (3)
O3	0.0155 (4)	0.0225 (4)	0.0195 (4)	0.0050 (3)	−0.0090 (3)	−0.0086 (3)
C1	0.0145 (6)	0.0203 (5)	0.0213 (5)	0.0036 (4)	−0.0041 (4)	−0.0069 (4)
C2	0.0192 (6)	0.0203 (5)	0.0260 (5)	0.0029 (5)	−0.0033 (5)	−0.0120 (4)
C3	0.0175 (6)	0.0214 (5)	0.0217 (5)	−0.0006 (5)	−0.0051 (4)	−0.0100 (4)
C4	0.0136 (6)	0.0188 (5)	0.0180 (5)	0.0007 (4)	−0.0030 (4)	−0.0050 (4)
C5	0.0150 (6)	0.0164 (5)	0.0170 (5)	0.0010 (4)	−0.0030 (4)	−0.0059 (4)
C6	0.0137 (6)	0.0160 (5)	0.0144 (4)	−0.0008 (4)	−0.0018 (4)	−0.0035 (4)
C7	0.0145 (6)	0.0150 (5)	0.0145 (4)	−0.0007 (4)	−0.0021 (4)	−0.0026 (4)
C8	0.0149 (6)	0.0190 (5)	0.0185 (5)	0.0021 (4)	−0.0031 (4)	−0.0058 (4)
C9	0.0143 (6)	0.0150 (5)	0.0167 (5)	0.0005 (4)	−0.0022 (4)	−0.0026 (4)
C10	0.0126 (6)	0.0160 (5)	0.0148 (4)	−0.0005 (4)	−0.0020 (4)	−0.0019 (4)
C11	0.0157 (6)	0.0171 (5)	0.0171 (5)	0.0008 (4)	−0.0016 (4)	−0.0059 (4)
C12	0.0149 (6)	0.0186 (5)	0.0157 (4)	0.0001 (4)	−0.0036 (4)	−0.0056 (4)
C13	0.0122 (5)	0.0168 (5)	0.0154 (4)	0.0013 (4)	−0.0034 (4)	−0.0027 (4)
C14	0.0148 (6)	0.0177 (5)	0.0183 (5)	0.0018 (4)	−0.0025 (4)	−0.0070 (4)
C15	0.0151 (6)	0.0184 (5)	0.0159 (5)	−0.0004 (4)	−0.0037 (4)	−0.0052 (4)
C16	0.0159 (6)	0.0189 (5)	0.0165 (5)	0.0008 (4)	−0.0058 (4)	−0.0051 (4)
C17	0.0140 (6)	0.0179 (5)	0.0172 (5)	0.0016 (4)	−0.0042 (4)	−0.0037 (4)
C18	0.0140 (6)	0.0177 (5)	0.0179 (5)	0.0018 (4)	−0.0052 (4)	−0.0043 (4)
C19	0.0139 (6)	0.0182 (5)	0.0173 (5)	0.0019 (4)	−0.0037 (4)	−0.0042 (4)
C20	0.0150 (6)	0.0185 (5)	0.0178 (5)	0.0023 (4)	−0.0043 (4)	−0.0051 (4)
C21	0.0147 (6)	0.0189 (5)	0.0167 (5)	0.0018 (4)	−0.0041 (4)	−0.0046 (4)
C22	0.0154 (6)	0.0182 (5)	0.0171 (5)	0.0013 (4)	−0.0048 (4)	−0.0046 (4)
C23	0.0154 (6)	0.0198 (5)	0.0166 (5)	0.0025 (4)	−0.0049 (4)	−0.0047 (4)
C24	0.0166 (6)	0.0180 (5)	0.0175 (5)	0.0022 (4)	−0.0050 (4)	−0.0043 (4)
C25	0.0166 (6)	0.0184 (5)	0.0181 (5)	0.0030 (4)	−0.0056 (4)	−0.0050 (4)
C26	0.0170 (6)	0.0174 (5)	0.0175 (5)	0.0018 (4)	−0.0056 (4)	−0.0044 (4)
C27	0.0190 (6)	0.0181 (5)	0.0202 (5)	0.0030 (5)	−0.0077 (4)	−0.0064 (4)
C28	0.0189 (6)	0.0216 (5)	0.0177 (5)	0.0021 (5)	−0.0063 (4)	−0.0058 (4)
C29	0.0220 (7)	0.0282 (6)	0.0269 (6)	0.0062 (5)	−0.0112 (5)	−0.0107 (5)

Geometric parameters (Å, º) top

O1—C4	1.3561 (14)	C18—C19	1.5239 (15)
O1—H1O1	0.927 (19)	C18—H18A	0.9700
O2—C7	1.2296 (13)	C18—H18B	0.9700
O3—C13	1.3594 (13)	C19—C20	1.5237 (15)
O3—C16	1.4346 (13)	C19—H19A	0.9700
C1—C2	1.3906 (16)	C19—H19B	0.9700
C1—C6	1.3958 (14)	C20—C21	1.5228 (15)
C1—H1A	0.9300	C20—H20A	0.9700
C2—C3	1.3799 (17)	C20—H20B	0.9700
C2—H2A	0.9300	C21—C22	1.5244 (15)
C3—C4	1.3959 (15)	C21—H21A	0.9700
C3—H3A	0.9300	C21—H21B	0.9700
C4—C5	1.3876 (15)	C22—C23	1.5205 (16)
C5—C6	1.3910 (16)	C22—H22A	0.9700
C5—H5A	0.9300	C22—H22B	0.9700
C6—C7	1.4977 (15)	C23—C24	1.5199 (15)
C7—C8	1.4642 (16)	C23—H23A	0.9700
C8—C9	1.3394 (15)	C23—H23B	0.9700
C8—H8A	0.9300	C24—C25	1.5208 (16)
C9—C10	1.4550 (16)	C24—H24A	0.9700
C9—H9A	0.9300	C24—H24B	0.9700
C10—C11	1.3960 (14)	C25—C26	1.5224 (15)
C10—C15	1.4041 (15)	C25—H25A	0.9700
C11—C12	1.3898 (16)	C25—H25B	0.9700
C11—H11A	0.9300	C26—C27	1.5210 (16)
C12—C13	1.3892 (14)	C26—H26A	0.9700
C12—H12A	0.9300	C26—H26B	0.9700
C13—C14	1.3996 (14)	C27—C28	1.5220 (15)
C14—C15	1.3728 (15)	C27—H27A	0.9700
C14—H14A	0.9300	C27—H27B	0.9700
C15—H15A	0.9300	C28—C29	1.5186 (17)
C16—C17	1.5133 (15)	C28—H28A	0.9700
C16—H16A	0.9700	C28—H28B	0.9700
C16—H16B	0.9700	C29—H29A	0.9600
C17—C18	1.5238 (15)	C29—H29B	0.9600
C17—H17A	0.9700	C29—H29C	0.9600
C17—H17B	0.9700

C4—O1—H1O1	109.7 (12)	C20—C19—H19A	108.6
C13—O3—C16	120.08 (8)	C18—C19—H19A	108.6
C2—C1—C6	119.72 (11)	C20—C19—H19B	108.6
C2—C1—H1A	120.1	C18—C19—H19B	108.6
C6—C1—H1A	120.1	H19A—C19—H19B	107.5
C3—C2—C1	120.77 (10)	C21—C20—C19	112.36 (9)
C3—C2—H2A	119.6	C21—C20—H20A	109.1
C1—C2—H2A	119.6	C19—C20—H20A	109.1
C2—C3—C4	119.90 (10)	C21—C20—H20B	109.1
C2—C3—H3A	120.1	C19—C20—H20B	109.1
C4—C3—H3A	120.1	H20A—C20—H20B	107.9
O1—C4—C5	122.73 (9)	C20—C21—C22	114.06 (9)
O1—C4—C3	117.87 (10)	C20—C21—H21A	108.7
C5—C4—C3	119.40 (10)	C22—C21—H21A	108.7
C4—C5—C6	120.95 (10)	C20—C21—H21B	108.7
C4—C5—H5A	119.5	C22—C21—H21B	108.7
C6—C5—H5A	119.5	H21A—C21—H21B	107.6
C5—C6—C1	119.26 (10)	C23—C22—C21	112.97 (9)
C5—C6—C7	117.38 (9)	C23—C22—H22A	109.0
C1—C6—C7	123.31 (10)	C21—C22—H22A	109.0
O2—C7—C8	121.41 (10)	C23—C22—H22B	109.0
O2—C7—C6	118.66 (10)	C21—C22—H22B	109.0
C8—C7—C6	119.91 (9)	H22A—C22—H22B	107.8
C9—C8—C7	121.35 (10)	C24—C23—C22	113.65 (9)
C9—C8—H8A	119.3	C24—C23—H23A	108.8
C7—C8—H8A	119.3	C22—C23—H23A	108.8
C8—C9—C10	126.83 (10)	C24—C23—H23B	108.8
C8—C9—H9A	116.6	C22—C23—H23B	108.8
C10—C9—H9A	116.6	H23A—C23—H23B	107.7
C11—C10—C15	117.57 (10)	C23—C24—C25	113.25 (9)
C11—C10—C9	119.95 (10)	C23—C24—H24A	108.9
C15—C10—C9	122.45 (10)	C25—C24—H24A	108.9
C12—C11—C10	122.27 (10)	C23—C24—H24B	108.9
C12—C11—H11A	118.9	C25—C24—H24B	108.9
C10—C11—H11A	118.9	H24A—C24—H24B	107.7
C13—C12—C11	118.83 (10)	C24—C25—C26	113.70 (9)
C13—C12—H12A	120.6	C24—C25—H25A	108.8
C11—C12—H12A	120.6	C26—C25—H25A	108.8
O3—C13—C12	125.69 (10)	C24—C25—H25B	108.8
O3—C13—C14	114.44 (9)	C26—C25—H25B	108.8
C12—C13—C14	119.86 (10)	H25A—C25—H25B	107.7
C15—C14—C13	120.53 (10)	C27—C26—C25	112.98 (9)
C15—C14—H14A	119.7	C27—C26—H26A	109.0
C13—C14—H14A	119.7	C25—C26—H26A	109.0
C14—C15—C10	120.92 (10)	C27—C26—H26B	109.0
C14—C15—H15A	119.5	C25—C26—H26B	109.0
C10—C15—H15A	119.5	H26A—C26—H26B	107.8
O3—C16—C17	104.86 (8)	C26—C27—C28	114.37 (9)
O3—C16—H16A	110.8	C26—C27—H27A	108.7
C17—C16—H16A	110.8	C28—C27—H27A	108.7
O3—C16—H16B	110.8	C26—C27—H27B	108.7
C17—C16—H16B	110.8	C28—C27—H27B	108.7
H16A—C16—H16B	108.9	H27A—C27—H27B	107.6
C16—C17—C18	114.84 (9)	C29—C28—C27	112.26 (9)
C16—C17—H17A	108.6	C29—C28—H28A	109.2
C18—C17—H17A	108.6	C27—C28—H28A	109.2
C16—C17—H17B	108.6	C29—C28—H28B	109.2
C18—C17—H17B	108.6	C27—C28—H28B	109.2
H17A—C17—H17B	107.5	H28A—C28—H28B	107.9
C17—C18—C19	110.54 (9)	C28—C29—H29A	109.5
C17—C18—H18A	109.5	C28—C29—H29B	109.5
C19—C18—H18A	109.5	H29A—C29—H29B	109.5
C17—C18—H18B	109.5	C28—C29—H29C	109.5
C19—C18—H18B	109.5	H29A—C29—H29C	109.5
H18A—C18—H18B	108.1	H29B—C29—H29C	109.5
C20—C19—C18	114.83 (9)

C6—C1—C2—C3	−0.31 (19)	C16—O3—C13—C12	−3.73 (17)
C1—C2—C3—C4	−0.14 (19)	C16—O3—C13—C14	176.57 (10)
C2—C3—C4—O1	−179.67 (11)	C11—C12—C13—O3	179.88 (11)
C2—C3—C4—C5	0.08 (18)	C11—C12—C13—C14	−0.44 (17)
O1—C4—C5—C6	−179.82 (11)	O3—C13—C14—C15	179.62 (10)
C3—C4—C5—C6	0.43 (18)	C12—C13—C14—C15	−0.09 (18)
C4—C5—C6—C1	−0.88 (18)	C13—C14—C15—C10	0.82 (18)
C4—C5—C6—C7	176.62 (10)	C11—C10—C15—C14	−0.98 (17)
C2—C1—C6—C5	0.81 (18)	C9—C10—C15—C14	177.11 (11)
C2—C1—C6—C7	−176.53 (11)	C13—O3—C16—C17	−179.19 (9)
C5—C6—C7—O2	−3.99 (16)	O3—C16—C17—C18	173.04 (9)
C1—C6—C7—O2	173.39 (11)	C16—C17—C18—C19	179.95 (10)
C5—C6—C7—C8	177.31 (10)	C17—C18—C19—C20	176.22 (10)
C1—C6—C7—C8	−5.30 (17)	C18—C19—C20—C21	179.98 (10)
O2—C7—C8—C9	−0.64 (18)	C19—C20—C21—C22	178.56 (10)
C6—C7—C8—C9	178.02 (11)	C20—C21—C22—C23	178.85 (10)
C7—C8—C9—C10	−177.78 (11)	C21—C22—C23—C24	179.19 (10)
C8—C9—C10—C11	−179.31 (12)	C22—C23—C24—C25	179.71 (10)
C8—C9—C10—C15	2.64 (19)	C23—C24—C25—C26	−179.99 (10)
C15—C10—C11—C12	0.44 (17)	C24—C25—C26—C27	−179.83 (10)
C9—C10—C11—C12	−177.70 (11)	C25—C26—C27—C28	−176.74 (10)
C10—C11—C12—C13	0.25 (18)	C26—C27—C28—C29	−177.78 (11)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	0.93 (2)	1.80 (2)	2.7269 (14)	175.6 (18)
C29—H29A···O1ⁱⁱ	0.96	2.44	3.3589 (18)	160
C17—H17B···Cg1ⁱⁱⁱ	0.97	2.73	3.6159 (16)	152
C28—H28A···Cg2^iv	0.97	2.93	3.8481 (16)	159

Symmetry codes: (i) −x+3, −y, −z+1; (ii) x−4, y+1, z−1; (iii) x−1, y, z; (iv) x−3, y+1, z−1.

Experimental details

Crystal data
Chemical formula	C₂₉H₄₀O₃
M_r	436.61
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.5138 (16), 10.155 (2), 19.264 (5)
α, β, γ (°)	75.361 (6), 85.872 (7), 83.013 (6)
V (Å³)	1222.6 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.29 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.979, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	26295, 7155, 5052
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.147, 0.95
No. of reflections	7155
No. of parameters	293
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.23

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C10–C15 and C1–C6 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	0.93 (2)	1.80 (2)	2.7269 (14)	175.6 (18)
C29—H29A···O1ⁱⁱ	0.9600	2.4400	3.3589 (18)	160.00
C17—H17B···Cg1ⁱⁱⁱ	0.9700	2.73	3.6159 (16)	152
C28—H28A···Cg2^iv	0.9700	2.93	3.8481 (16)	159

Symmetry codes: (i) −x+3, −y, −z+1; (ii) x−4, y+1, z−1; (iii) x−1, y, z; (iv) x−3, y+1, z−1.

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

IAR and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171. ZN and HH thank Universiti Malaysia Sarawak and the Ministry of Science, Technology and Innovation (MOSTI), for financing this project through FRGS/01(14)/743/2010 (29). SMHF thanks the Malaysian Government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.

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Volume 68| Part 10| October 2012| Pages o2911-o2912

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