11,12-Dihy­droxy-10,6,8,11,13-icetexapentan-1-one

Razak, I.A.; Chantrapromma, S.; Salae, A.W.; Fun, H.-K.

doi:10.1107/S1600536810053754

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o256-o257

doi:10.1107/S1600536810053754

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11,12-Dihydroxy-10,6,8,11,13-icetexapentan-1-one

Ibrahim Abdul Razak,^a Suchada Chantrapromma,^b ‡ Abdul Wahab Salae ^b and Hoong-Kun Fun ^a ^*§

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 19 December 2010; accepted 22 December 2010; online 8 January 2011)

The title compound [systematic name: 14,15-dihydroxy-7,7-dimethyl-13-(propan-2-yl)tricyclo[9.4.0.0^3,8]pentadeca-1(11),3(8),9,12,14-pentaen-4-one], C₂₀H₂₄O₃, is a new icetexane diterpenoid which was isolated from the roots of Premna obtusifolia (Verbenaceae). The molecule has three fused rings: a cyclohexenone, a central cycloheptene and a benzene ring. The cyclohexenone ring is in an envelope conformation, whereas the cycloheptene ring is in a twisted boat conformation. Intramolecular O—H⋯O hydrogen bonds generate S(5) and S(8) ring motifs. In the crystal, molecules are linked into dimers through O—H⋯O hydrogen bonds. These dimers are arranged in to sheets parallel to the ac plane. C—H⋯O and weak C—H⋯π interactions are also present.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ) and for ring conformations, see: Cremer & Pople (1975 ). For bond-length data, see: Allen et al. (1987 ). For background to Verbenaceae plants and the bioactivity of icetexane, see: Bunluepuech & Tewtrakul (2009 ); Hymavathi et al. (2009 ); Simmons & Sarpong (2009 ). For related structures, see: Asik et al. (2010 ); Razak et al. (2010 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₂₄O₃
M_r = 312.39
Monoclinic, C 2/c
a = 25.1090 (9) Å
b = 9.4317 (3) Å
c = 14.9609 (4) Å
β = 108.683 (2)°
V = 3356.35 (19) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.60 × 0.32 × 0.28 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.953, T_max = 0.977
60861 measured reflections
7404 independent reflections
6198 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.125
S = 1.03
7404 reflections
304 parameters
All H-atom parameters refined
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C8–C9/C11–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.870 (18)	2.088 (18)	2.9479 (8)	169.8 (15)
O2—H1O2⋯O2ⁱ	0.870 (18)	2.541 (16)	2.8818 (7)	104.3 (12)
O3—H1O3⋯O2	0.875 (14)	2.208 (16)	2.6955 (7)	114.9 (12)
O3—H1O3⋯O1ⁱ	0.875 (14)	2.046 (14)	2.8448 (7)	151.3 (14)
C7—H7A⋯O2ⁱⁱ	0.974 (12)	2.440 (12)	3.2262 (9)	137.5 (10)
C15—H15A⋯O3	1.007 (15)	2.364 (15)	2.8216 (8)	106.6 (10)
C18—H18B⋯O3ⁱⁱⁱ	0.986 (15)	2.585 (15)	3.3467 (10)	134.1 (11)
C19—H19B⋯Cg1ⁱⁱ	1.011 (15)	2.798 (16)	3.7130 (10)	150.8 (12)
C20—H20A⋯Cg1^iv	0.993 (11)	2.847 (12)	3.7506 (8)	151.6 (9)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x, -y-1, z-{\script{1\over 2}}]$ .

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/S1600536810053754/ng5091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810053754/ng5091Isup2.hkl

checkCIF report

Comment top

The extracts of Verbenaceae plants have been found to possess anti-HIV-1 integrase activity (Bunluepuech & Tewtrakul, 2009). Premna obtusifolia (Verbenaceae), a small tree found in the mangrove forests, is one of the Verbenaceae plants. As part of our research on bioactive compounds from medicinal plants, we previouly reported the crystal structures of diterpenoids from the roots of Premna obtusifolia (Verbenaceae) which was collected from Satun province in the southern of Thailand (Asik et al., 2010; Razak et al., 2010). The title icetexane diterpenoid (I), also named as Obtusin N, is a new compound which was isolated from the same plant. The icetexane diterpenoids encompass a variety of bioactive and structurally interesting compounds (Hymavathi et al., 2009; Simmons & Sarpong, 2009). We herein report the crystal structure of (I).

The molecule of (I) has a tricyclic skeleton (Fig. 1). The cyclohexene ring (C1–C5/C10) is in an envelope conformation with the puckering C3 atom having a deviation of 0.3373 (9) Å and puckering parameters Q = 0.4877 (9) Å, θ = 65.14 (19)° and ϕ = 113.04 (11)° (Cremer & Pople, 1975) whereas the central cycloheptene ring (C5–C10/C20) is in twisted-boat conformation with the most puckering atom C20 having deviation of 0.5665 (8) Å and puckering parameter Q = 0.8294 (8) Å. The benzene ring (C8–C9/C11–C14) is slightly twisted with the maximum deviation of -0.0575 (7) and 0.0388 (7) Å for atoms C9 and C11, respectively. The two hydroxy groups are co-planar with the attached benzene ring with r.m.s. deviation of 0.026 (7) Å. The orientation of the propanyl group is described by the torsion angles C14–C13–C15–C16 = 81.62 (9)° and C14–C13–C15–C17 = -42.19 (10)°. Intramolecular O3—H1O3···O2 and O2—H1O2···O1 hydrogen bonds (Table 1) generate S(5) and S(8) ring motifs, respectively (Fig. 1) (Bernstein et al., 1995). The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable to the related structures (Asik et al., 2010; Razak et al., 2010).

The crystal packing of (I) is stabilized by intermolecular O—H···O hydrogen bonds, C—H···O and C—H···π weak interactions (Fig. 2 and Table 1). The molecules are linked into dimers through O3—H1O3···O1 hydrogen bonds (Table 1 and Fig. 2). These dimers are arranged into sheets parallel to the ac plane. C—H···π weak interactions were presented (Table 1).

Related literature top

For details of hydrogen-bond motifs, see: Bernstein et al. (1995) and for ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For background to Verbenaceae plants and the bioactivity of icetexane, see: Bunluepuech & Tewtrakul (2009); Hymavathi et al. (2009); Simmons & Sarpong (2009). For related structures, see: Asik et al. (2010); Razak et al. (2010). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).

Experimental top

The air-dried roots of premna obtusifolia (4.5 kg) were extracted with hexane (2 x 20 L) at room temperature. The combined extracts were concentrated under reduced pressure to afford a dark yellow extract (40.0 g) which was subjected to quick column chromatography (QCC) over silica gel using solvents of increasing polarity from n-hexane to EtOAc to afford 7 fractions (F1—F7). Fraction F6 was further purified by quick column chromatography (QCC) using n-hexane-ETOAc (9:1), yielding the title compound (87.3 mg). Yellow needle-shaped single crystals of the title compound suitable for x-ray structure determination were recrystallized from n-hexane after several days.

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 structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. Intramolecular O—H···O hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of (I) viewed along the b axis, showing sheets parallel to the ac plane. Hydrogen bonds are shown as dashed lines.

14,15-dihydroxy-7,7-dimethyl-13-(propan-2-yl)tricyclo[9.4.0.0^3,8]pentadeca- 1(11),3(8),9,12,14-pentaen-4-one top

Crystal data top

C₂₀H₂₄O₃	F(000) = 1344
M_r = 312.39	D_x = 1.236 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7404 reflections
a = 25.1090 (9) Å	θ = 2.3–35.0°
b = 9.4317 (3) Å	µ = 0.08 mm⁻¹
c = 14.9609 (4) Å	T = 100 K
β = 108.683 (2)°	Needle, yellow
V = 3356.35 (19) Å³	0.60 × 0.32 × 0.28 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	7404 independent reflections
Radiation source: sealed tube	6198 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 35.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −38→40
T_min = 0.953, T_max = 0.977	k = −14→15
60861 measured reflections	l = −24→24

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	All H-atom parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0755P)² + 1.0087P] where P = (F_o² + 2F_c²)/3
7404 reflections	(Δ/σ)_max = 0.001
304 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₄O₃	V = 3356.35 (19) Å³
M_r = 312.39	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.1090 (9) Å	µ = 0.08 mm⁻¹
b = 9.4317 (3) Å	T = 100 K
c = 14.9609 (4) Å	0.60 × 0.32 × 0.28 mm
β = 108.683 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	7404 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6198 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.977	R_int = 0.029
60861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.125	All H-atom parameters refined
S = 1.03	Δρ_max = 0.48 e Å⁻³
7404 reflections	Δρ_min = −0.21 e Å⁻³
304 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	0.34135 (2)	0.18997 (7)	0.45441 (4)	0.02727 (13)
O2	0.22121 (2)	0.14713 (6)	0.42998 (3)	0.02042 (11)
H1O2	0.2573 (7)	0.1602 (17)	0.4448 (11)	0.048 (4)*
O3	0.11523 (2)	0.24175 (6)	0.35038 (3)	0.01917 (10)
H1O3	0.1377 (6)	0.2421 (15)	0.4088 (10)	0.041 (4)*
C1	0.35660 (3)	0.18067 (8)	0.38355 (5)	0.02009 (13)
C2	0.40308 (3)	0.27126 (10)	0.37203 (6)	0.02604 (15)
H2A	0.4322 (6)	0.2867 (15)	0.4357 (10)	0.038 (3)*
H2B	0.3867 (6)	0.3655 (16)	0.3534 (10)	0.040 (3)*
C3	0.42779 (3)	0.20818 (9)	0.30042 (6)	0.02461 (14)
H3A	0.4475 (5)	0.1170 (14)	0.3235 (9)	0.031 (3)*
H3B	0.4575 (6)	0.2728 (14)	0.2903 (9)	0.035 (3)*
C4	0.38338 (3)	0.17810 (8)	0.20403 (5)	0.01959 (12)
C5	0.33387 (3)	0.09795 (7)	0.21853 (5)	0.01718 (11)
C6	0.29158 (3)	0.04077 (8)	0.13478 (5)	0.02060 (13)
H6A	0.3058 (5)	0.0138 (14)	0.0831 (9)	0.030 (3)*
C7	0.23475 (3)	0.03856 (8)	0.11708 (5)	0.02164 (13)
H7A	0.2123 (5)	0.0114 (13)	0.0533 (8)	0.027 (3)*
C8	0.20317 (3)	0.08458 (7)	0.17837 (4)	0.01703 (11)
C9	0.22671 (3)	0.07722 (7)	0.27714 (4)	0.01548 (11)
C10	0.32690 (3)	0.08736 (7)	0.30526 (4)	0.01682 (11)
C11	0.19897 (3)	0.14125 (7)	0.33345 (4)	0.01495 (11)
C12	0.14429 (3)	0.19365 (7)	0.29375 (4)	0.01505 (11)
C13	0.11813 (3)	0.19232 (7)	0.19542 (4)	0.01734 (11)
C14	0.14864 (3)	0.14018 (8)	0.13931 (5)	0.01940 (12)
H14A	0.1327 (5)	0.1435 (13)	0.0691 (8)	0.029 (3)*
C15	0.05752 (3)	0.24151 (8)	0.15458 (5)	0.02181 (13)
H15A	0.0487 (6)	0.3020 (16)	0.2035 (10)	0.043 (4)*
C16	0.01786 (3)	0.11352 (11)	0.13660 (7)	0.03109 (18)
H16A	0.0246 (6)	0.0563 (16)	0.0858 (10)	0.041 (3)*
H16B	−0.0208 (6)	0.1452 (14)	0.1209 (10)	0.038 (3)*
H16C	0.0246 (6)	0.0539 (16)	0.1939 (10)	0.043 (4)*
C17	0.04657 (4)	0.32889 (10)	0.06447 (7)	0.03084 (17)
H17A	0.0749 (7)	0.4078 (17)	0.0732 (11)	0.051 (4)*
H17B	0.0075 (6)	0.3743 (15)	0.0475 (10)	0.040 (3)*
H17C	0.0477 (6)	0.2691 (16)	0.0078 (10)	0.043 (4)*
C18	0.41211 (4)	0.08869 (9)	0.14665 (6)	0.02682 (15)
H18A	0.3865 (6)	0.0729 (15)	0.0807 (10)	0.036 (3)*
H18B	0.4239 (6)	−0.0029 (16)	0.1787 (9)	0.039 (3)*
H18C	0.4464 (5)	0.1393 (14)	0.1442 (9)	0.034 (3)*
C19	0.36195 (4)	0.31667 (9)	0.15095 (7)	0.03147 (17)
H19A	0.3940 (6)	0.3712 (17)	0.1398 (11)	0.048 (4)*
H19B	0.3440 (6)	0.3764 (17)	0.1896 (10)	0.045 (4)*
H19C	0.3354 (6)	0.2977 (15)	0.0893 (10)	0.037 (3)*
C20	0.28082 (3)	−0.00267 (7)	0.31829 (5)	0.01867 (12)
H20A	0.2799 (5)	−0.0936 (12)	0.2844 (8)	0.022 (3)*
H20B	0.2880 (4)	−0.0209 (12)	0.3870 (8)	0.022 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0226 (2)	0.0428 (3)	0.0156 (2)	0.0040 (2)	0.00490 (18)	−0.0048 (2)
O2	0.0181 (2)	0.0313 (3)	0.01191 (19)	0.00406 (19)	0.00491 (16)	0.00394 (17)
O3	0.0166 (2)	0.0264 (2)	0.0148 (2)	0.00275 (17)	0.00536 (16)	−0.00128 (17)
C1	0.0154 (3)	0.0273 (3)	0.0159 (3)	0.0042 (2)	0.0026 (2)	−0.0018 (2)
C2	0.0178 (3)	0.0336 (4)	0.0254 (3)	−0.0039 (3)	0.0051 (2)	−0.0100 (3)
C3	0.0174 (3)	0.0287 (4)	0.0284 (3)	−0.0002 (2)	0.0082 (2)	−0.0037 (3)
C4	0.0206 (3)	0.0185 (3)	0.0220 (3)	0.0002 (2)	0.0100 (2)	−0.0002 (2)
C5	0.0178 (3)	0.0177 (3)	0.0167 (2)	0.0012 (2)	0.0065 (2)	−0.0009 (2)
C6	0.0210 (3)	0.0246 (3)	0.0174 (3)	0.0002 (2)	0.0078 (2)	−0.0051 (2)
C7	0.0210 (3)	0.0267 (3)	0.0172 (3)	0.0002 (2)	0.0061 (2)	−0.0069 (2)
C8	0.0169 (2)	0.0185 (3)	0.0154 (2)	−0.0007 (2)	0.0048 (2)	−0.0037 (2)
C9	0.0155 (2)	0.0155 (2)	0.0158 (2)	0.00006 (19)	0.00547 (19)	0.00067 (19)
C10	0.0154 (2)	0.0197 (3)	0.0151 (2)	0.0027 (2)	0.00442 (19)	0.0006 (2)
C11	0.0157 (2)	0.0166 (2)	0.0127 (2)	0.00038 (19)	0.00469 (18)	0.00190 (19)
C12	0.0152 (2)	0.0160 (2)	0.0140 (2)	−0.00001 (19)	0.00473 (19)	−0.00030 (18)
C13	0.0156 (2)	0.0200 (3)	0.0147 (2)	0.0005 (2)	0.00235 (19)	−0.0028 (2)
C14	0.0182 (3)	0.0241 (3)	0.0143 (2)	−0.0001 (2)	0.0030 (2)	−0.0046 (2)
C15	0.0183 (3)	0.0285 (3)	0.0157 (3)	0.0051 (2)	0.0013 (2)	−0.0036 (2)
C16	0.0164 (3)	0.0421 (5)	0.0334 (4)	−0.0012 (3)	0.0060 (3)	0.0097 (3)
C17	0.0259 (4)	0.0298 (4)	0.0305 (4)	0.0017 (3)	0.0002 (3)	0.0083 (3)
C18	0.0278 (3)	0.0259 (3)	0.0338 (4)	−0.0016 (3)	0.0198 (3)	−0.0033 (3)
C19	0.0345 (4)	0.0222 (3)	0.0384 (4)	0.0030 (3)	0.0126 (4)	0.0088 (3)
C20	0.0184 (3)	0.0186 (3)	0.0201 (3)	0.0032 (2)	0.0077 (2)	0.0038 (2)

Geometric parameters (Å, º) top

O1—C1	1.2403 (9)	C9—C20	1.5022 (9)
O2—C11	1.3725 (8)	C10—C20	1.4976 (9)
O2—H1O2	0.869 (16)	C11—C12	1.3998 (9)
O3—C12	1.3610 (8)	C12—C13	1.4058 (9)
O3—H1O3	0.875 (14)	C13—C14	1.3948 (9)
C1—C10	1.4638 (10)	C13—C15	1.5196 (9)
C1—C2	1.5003 (11)	C14—H14A	0.997 (12)
C2—C3	1.5208 (11)	C15—C17	1.5280 (12)
C2—H2A	1.008 (14)	C15—C16	1.5329 (12)
C2—H2B	0.982 (15)	C15—H15A	1.006 (15)
C3—C4	1.5406 (11)	C16—H16A	0.989 (14)
C3—H3A	0.996 (13)	C16—H16B	0.969 (14)
C3—H3B	1.011 (13)	C16—H16C	0.993 (15)
C4—C5	1.5286 (10)	C17—H17A	1.008 (16)
C4—C19	1.5345 (11)	C17—H17B	1.026 (14)
C4—C18	1.5379 (10)	C17—H17C	1.026 (15)
C5—C10	1.3674 (9)	C18—H18A	1.001 (13)
C5—C6	1.4615 (10)	C18—H18B	0.987 (15)
C6—C7	1.3655 (10)	C18—H18C	0.996 (13)
C6—H6A	0.984 (12)	C19—H19A	1.013 (15)
C7—C8	1.4574 (9)	C19—H19B	1.011 (15)
C7—H7A	0.975 (12)	C19—H19C	0.966 (14)
C8—C9	1.4065 (9)	C20—H20A	0.993 (11)
C8—C14	1.4068 (9)	C20—H20B	1.000 (11)
C9—C11	1.3912 (9)

C11—O2—H1O2	108.3 (10)	O3—C12—C13	119.36 (6)
C12—O3—H1O3	108.7 (9)	C11—C12—C13	120.46 (6)
O1—C1—C10	120.59 (7)	C14—C13—C12	118.06 (6)
O1—C1—C2	121.49 (7)	C14—C13—C15	122.54 (6)
C10—C1—C2	117.78 (6)	C12—C13—C15	119.35 (6)
C1—C2—C3	111.47 (6)	C13—C14—C8	122.04 (6)
C1—C2—H2A	109.2 (8)	C13—C14—H14A	120.7 (7)
C3—C2—H2A	112.7 (8)	C8—C14—H14A	117.3 (7)
C1—C2—H2B	106.1 (8)	C13—C15—C17	113.17 (6)
C3—C2—H2B	112.5 (8)	C13—C15—C16	109.93 (6)
H2A—C2—H2B	104.4 (11)	C17—C15—C16	110.29 (6)
C2—C3—C4	113.28 (6)	C13—C15—H15A	107.8 (8)
C2—C3—H3A	111.3 (7)	C17—C15—H15A	108.4 (9)
C4—C3—H3A	107.2 (7)	C16—C15—H15A	107.0 (9)
C2—C3—H3B	110.9 (7)	C15—C16—H16A	107.6 (8)
C4—C3—H3B	108.5 (7)	C15—C16—H16B	110.0 (8)
H3A—C3—H3B	105.3 (10)	H16A—C16—H16B	112.7 (11)
C5—C4—C19	109.16 (6)	C15—C16—H16C	111.9 (8)
C5—C4—C18	110.87 (6)	H16A—C16—H16C	109.3 (12)
C19—C4—C18	109.12 (7)	H16B—C16—H16C	105.3 (11)
C5—C4—C3	109.63 (6)	C15—C17—H17A	111.3 (9)
C19—C4—C3	110.87 (7)	C15—C17—H17B	109.3 (8)
C18—C4—C3	107.17 (6)	H17A—C17—H17B	107.7 (12)
C10—C5—C6	120.53 (6)	C15—C17—H17C	112.8 (8)
C10—C5—C4	121.86 (6)	H17A—C17—H17C	108.0 (12)
C6—C5—C4	117.47 (6)	H17B—C17—H17C	107.6 (11)
C7—C6—C5	126.80 (6)	C4—C18—H18A	111.3 (8)
C7—C6—H6A	117.7 (7)	C4—C18—H18B	109.3 (8)
C5—C6—H6A	114.9 (7)	H18A—C18—H18B	110.3 (11)
C6—C7—C8	128.23 (6)	C4—C18—H18C	108.9 (8)
C6—C7—H7A	115.8 (7)	H18A—C18—H18C	109.0 (10)
C8—C7—H7A	115.7 (7)	H18B—C18—H18C	108.0 (11)
C9—C8—C14	118.71 (6)	C4—C19—H19A	110.6 (9)
C9—C8—C7	121.08 (6)	C4—C19—H19B	109.0 (9)
C14—C8—C7	120.20 (6)	H19A—C19—H19B	109.6 (12)
C11—C9—C8	119.44 (6)	C4—C19—H19C	110.9 (8)
C11—C9—C20	122.14 (6)	H19A—C19—H19C	106.1 (12)
C8—C9—C20	118.41 (6)	H19B—C19—H19C	110.6 (12)
C5—C10—C1	121.89 (6)	C10—C20—C9	107.30 (5)
C5—C10—C20	120.26 (6)	C10—C20—H20A	108.4 (6)
C1—C10—C20	116.97 (6)	C9—C20—H20A	110.8 (6)
O2—C11—C9	122.74 (6)	C10—C20—H20B	109.8 (6)
O2—C11—C12	116.45 (5)	C9—C20—H20B	110.4 (6)
C9—C11—C12	120.63 (6)	H20A—C20—H20B	110.1 (9)
O3—C12—C11	120.14 (5)

O1—C1—C2—C3	160.07 (7)	O1—C1—C10—C20	−4.42 (10)
C10—C1—C2—C3	−24.13 (10)	C2—C1—C10—C20	179.74 (6)
C1—C2—C3—C4	54.32 (9)	C8—C9—C11—O2	−175.30 (6)
C2—C3—C4—C5	−48.51 (9)	C20—C9—C11—O2	5.92 (10)
C2—C3—C4—C19	72.08 (9)	C8—C9—C11—C12	9.76 (9)
C2—C3—C4—C18	−168.92 (7)	C20—C9—C11—C12	−169.02 (6)
C19—C4—C5—C10	−108.14 (8)	O2—C11—C12—O3	−2.53 (9)
C18—C4—C5—C10	131.62 (7)	C9—C11—C12—O3	172.71 (6)
C3—C4—C5—C10	13.49 (9)	O2—C11—C12—C13	179.82 (6)
C19—C4—C5—C6	67.64 (8)	C9—C11—C12—C13	−4.93 (10)
C18—C4—C5—C6	−52.61 (8)	O3—C12—C13—C14	−178.92 (6)
C3—C4—C5—C6	−170.74 (6)	C11—C12—C13—C14	−1.26 (10)
C10—C5—C6—C7	35.04 (12)	O3—C12—C13—C15	−1.36 (10)
C4—C5—C6—C7	−140.79 (8)	C11—C12—C13—C15	176.30 (6)
C5—C6—C7—C8	−3.68 (14)	C12—C13—C14—C8	2.58 (11)
C6—C7—C8—C9	−29.82 (12)	C15—C13—C14—C8	−174.89 (7)
C6—C7—C8—C14	148.89 (8)	C9—C8—C14—C13	2.18 (10)
C14—C8—C9—C11	−8.32 (10)	C7—C8—C14—C13	−176.55 (7)
C7—C8—C9—C11	170.41 (6)	C14—C13—C15—C17	−42.19 (10)
C14—C8—C9—C20	170.51 (6)	C12—C13—C15—C17	140.37 (7)
C7—C8—C9—C20	−10.77 (9)	C14—C13—C15—C16	81.62 (9)
C6—C5—C10—C1	−159.14 (6)	C12—C13—C15—C16	−95.82 (8)
C4—C5—C10—C1	16.50 (10)	C5—C10—C20—C9	−75.85 (8)
C6—C5—C10—C20	9.77 (10)	C1—C10—C20—C9	93.60 (7)
C4—C5—C10—C20	−174.58 (6)	C11—C9—C20—C10	−106.68 (7)
O1—C1—C10—C5	164.85 (7)	C8—C9—C20—C10	74.52 (7)
C2—C1—C10—C5	−10.99 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of C8–C9/C11–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.870 (18)	2.088 (18)	2.9479 (8)	169.8 (15)
O2—H1O2···O2ⁱ	0.870 (18)	2.541 (16)	2.8818 (7)	104.3 (12)
O3—H1O3···O2	0.875 (14)	2.208 (16)	2.6955 (7)	114.9 (12)
O3—H1O3···O1ⁱ	0.875 (14)	2.046 (14)	2.8448 (7)	151.3 (14)
C7—H7A···O2ⁱⁱ	0.974 (12)	2.440 (12)	3.2262 (9)	137.5 (10)
C15—H15A···O3	1.007 (15)	2.364 (15)	2.8216 (8)	106.6 (10)
C18—H18B···O3ⁱⁱⁱ	0.986 (15)	2.585 (15)	3.3467 (10)	134.1 (11)
C19—H19B···Cg1ⁱⁱ	1.011 (15)	2.798 (16)	3.7130 (10)	150.8 (12)
C20—H20A···Cg1^iv	0.993 (11)	2.847 (12)	3.7506 (8)	151.6 (9)

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄O₃
M_r	312.39
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	25.1090 (9), 9.4317 (3), 14.9609 (4)
β (°)	108.683 (2)
V (Å³)	3356.35 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.60 × 0.32 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.953, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	60861, 7404, 6198
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.125, 1.03
No. of reflections	7404
No. of parameters	304
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.21

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 C8–C9/C11–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.870 (18)	2.088 (18)	2.9479 (8)	169.8 (15)
O2—H1O2···O2ⁱ	0.870 (18)	2.541 (16)	2.8818 (7)	104.3 (12)
O3—H1O3···O2	0.875 (14)	2.208 (16)	2.6955 (7)	114.9 (12)
O3—H1O3···O1ⁱ	0.875 (14)	2.046 (14)	2.8448 (7)	151.3 (14)
C7—H7A···O2ⁱⁱ	0.974 (12)	2.440 (12)	3.2262 (9)	137.5 (10)
C15—H15A···O3	1.007 (15)	2.364 (15)	2.8216 (8)	106.6 (10)
C18—H18B···O3ⁱⁱⁱ	0.986 (15)	2.585 (15)	3.3467 (10)	134.1 (11)
C19—H19B···Cg1ⁱⁱ	1.011 (15)	2.798 (16)	3.7130 (10)	150.8 (12)
C20—H20A···Cg1^iv	0.993 (11)	2.847 (12)	3.7506 (8)	151.6 (9)

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

SC and AWS thank the Prince of Songkla University for financial support. The authors thank Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811151.

References

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Volume 67| Part 2| February 2011| Pages o256-o257

doi:10.1107/S1600536810053754

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