Acanthoic acid

Suwancharoen, S.; Tommeurd, W.; Phurat, C.; Muangsin, N.; Pornpakakul, S.

doi:10.1107/S1600536810019483

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1531

doi:10.1107/S1600536810019483

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Acanthoic acid

Sunisa Suwancharoen,^a Wantanee Tommeurd,^a Chuttree Phurat,^a Nongnuj Muangsin ^a and Surachai Pornpakakul ^a ^*

^aResearch Centre of Bioorganic Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok 10330, Thailand
^*Correspondence e-mail: nongnuj.j@chula.ac.th

(Received 4 May 2010; accepted 24 May 2010; online 5 June 2010)

The title compound [systematic name: (1R,4aR,7S,8aS,10aS)-1,4a,7-trimethyl-7-vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid], C₂₀H₃₀O₂, is a pimarane-type diterpene extracted from Croton oblongifolius. There are two independent molecules in the asymmetric unit. In both of these, the six-membered rings A, B and C adopt chair, boat and half-chair conformations, respectively. Rings A and B are trans-fused. The two molecules in the asymmetric unit form O—H⋯O hydrogen-bonded R₂²(8) dimers. The absolute configuration was assigned on the basis of the published literature on analogous structures.

Related literature

For background to the structure of acanthoic acid, see: Kim et al. (1998 ); Ling et al. (2001 ); Suh et al. (2001 ). For the related absolute configuration, see: Ling et al. (2000 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₃₀O₂
M_r = 302.44
Tetragonal, P 4₃
a = 12.8697 (16) Å
c = 21.768 (2) Å
V = 3605.5 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.40 × 0.20 × 0.02 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
21616 measured reflections
4824 independent reflections
3830 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.158
S = 1.02
4824 reflections
405 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.37 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
O2′—H2′⋯O1	0.82	1.87	2.687 (3)	177
O2—H2⋯O1′	0.82	1.83	2.649 (3)	175

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019483/fj2300sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810019483/fj2300Isup2.hkl

checkCIF report

Comment top

Acanthoic acid is a pimarane-type diterpene. It was first isolated from root bark of Acanthopanax koreanum Nakai (Araliaceae) (Kim et al., 1998) which has been used for treatment of neuralgia, hypertension, rheumatism and diabetes (Ling et al., 2001). This natural product exhibits anti-inflammatory activity (Suh et al., 2001). In this work, acanthoic acid was isolated in high yield from stem bark of Croton oblongifolius from Ratchaburi Province, Thailand.

There are two independent molecules in the asymmetric unit. In both independent molecules, the six memberred rings A, B and C adopts a chair, boat and half-chair conformations, respectively with the puckering parameters: Q = 0.546 Å, θ = 179.5° and ϕ = -107.0° for A, Q = 0.766 Å, θ = 89.9° and ϕ = -73.3° for B and Q = 0.493 Å, θ = 128.4° and ϕ = 35.2° for C. Rings A/B is trans-fused. The ethylene group substituted at C13 is in an equatorial position. The two molecules in the asymmetric unit form O—H···O hydrogen-bonded R₂²(8) dimers. The absolute configuration was assigned by comparison with the crystal structure of p-bromobenzoate ester-acanthoic derivative (Ling et al., 2000).

Related literature top

For background to the structures of acanthoic acid, see: Kim et al. (1998); Ling et al. (2001); Suh et al. (2001). For the related absolute configuration, see: Ling et al., (2000). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Dried powder of stem bark of Croton oblongifolius Roxb. (5.23 kg) from Ratchaburi province was extracted with hexane (4Lx5). The hexane crude extract was obtained as viscous yellow brown oil. This crude extract was purified by quick column chromatography on silica gel using a mixture of hexane and ethyl acetate (100:0-0:100). Fractions with similar components were combined according to TLC profile. The combined fraction eluted with a 7:3 mixture of hexane and ethyl acetate was crystallized in hexane and ethyl acetate to give colourless crystals (5.5% yield).

mp. 140-142^oC; [a]²⁵_D -36.1 (c = 0.42, benzene); ¹H-NMR (400 MHz, CDCl₃) d 5.81 (dd, 1H, J=10.6, 17.4 Hz, H-15), 5.39 (m, 1H, H-11), 4.93 (dd, 1H, J=1.2, 17.4 Hz, H-16 trans), 4.86 (dd, 1H, J=1.2, 10.6 Hz, H-16 cis), 2.31 (m, 1H, H-8), 2.21 (m, 1H, H-2 b), 2.15 (m, 1H, H-3a), 2.01 (m, 1H, H-12a), 1.93 (m, 1H, H-2a), 1.89 (m, 1H, H-6 b), 1.81 (m, 1H, H-1a), 1.77 (m, 1H, H-12 b), 1.73 (m, 1H, H-7a), 1.66 (dd, 1H, J=6.2, 13.0 Hz, H-5), 1.48 (m, 1H, H-6a), 1.45 (m, 1H, H-14a), 1.28 (m, 1H, H-1 b), 1.25 (s, 3H, H-18), 1.21 (m, 1H, H-7 b), 1.05 (m, 1H, H-3 b), 1.03 (m, 1H, H-14 b), 0.99 (s, 3H, H-20), 0.96 (s, 3H, H-17); ¹³C NMR (100 MHz, CDCl₃) d 184.60 (C-19), 150.23 (C-15), 149.85 (C-9), 116.59 (C-11), 109.16 (C-16), 47.99 (C-5), 44.21 (C-4), 41.92 (C-1), 41.80 (C-14), 38.43 (C-10), 38.08 (C-3), 37.47 (C-12), 34.86 (C-13), 28.67 (C-8), 28.56 (C-18), 27.76 (C-7), 22.40 (C-20), 22.17 (C-17), 20.34 (C-6), 18.91 (C-2)

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The asymmetric unit of the title compound showing two independent molecules. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal structure of the title compound viewed along the a-axis.

(1R,4aR,7S,8aS,10aS)-1,4a,7-trimethyl-7- vinyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid top

Crystal data top

C₂₀H₃₀O₂	D_x = 1.114 Mg m⁻³
M_r = 302.44	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃	Cell parameters from 9639 reflections
Hall symbol: P 4cw	θ = 1.6–30.2°
a = 12.8697 (16) Å	µ = 0.07 mm⁻¹
c = 21.768 (2) Å	T = 100 K
V = 3605.5 (7) Å³	Needle, colourless
Z = 8	0.40 × 0.20 × 0.02 mm
F(000) = 1328

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3830 reflections with I > 2σ(I)
Radiation source: Mo	R_int = 0.050
Graphite monochromator	θ_max = 30.2°, θ_min = 1.6°
ϕ and ω scans	h = −16→16
21616 measured reflections	k = −17→17
4824 independent reflections	l = −25→28

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.056	w = 1/[σ²(F_o²) + (0.0853P)² + 1.0669P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.158	(Δ/σ)_max = 0.002
S = 1.02	Δρ_max = 0.37 e Å⁻³
4824 reflections	Δρ_min = −0.29 e Å⁻³
405 parameters

Crystal data top

C₂₀H₃₀O₂	Z = 8
M_r = 302.44	Mo Kα radiation
Tetragonal, P4₃	µ = 0.07 mm⁻¹
a = 12.8697 (16) Å	T = 100 K
c = 21.768 (2) Å	0.40 × 0.20 × 0.02 mm
V = 3605.5 (7) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3830 reflections with I > 2σ(I)
21616 measured reflections	R_int = 0.050
4824 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	1 restraint
wR(F²) = 0.158	H-atom parameters constrained
S = 1.02	Δρ_max = 0.37 e Å⁻³
4824 reflections	Δρ_min = −0.29 e Å⁻³
405 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2020 (3)	0.6538 (3)	0.07071 (16)	0.0369 (7)
H1A	0.133	0.6753	0.0833	0.044*
H1B	0.208	0.6659	0.0269	0.044*
C2	0.2143 (3)	0.5365 (3)	0.08320 (18)	0.0395 (8)
H2A	0.1582	0.4991	0.0633	0.047*
H2B	0.2793	0.5125	0.0657	0.047*
C3	0.2130 (3)	0.5131 (3)	0.15123 (18)	0.0389 (7)
H3A	0.2246	0.4393	0.157	0.047*
H3B	0.1446	0.5293	0.1673	0.047*
C4	0.2946 (2)	0.5735 (2)	0.18865 (14)	0.0283 (6)
C5	0.2819 (2)	0.6927 (2)	0.17370 (13)	0.0257 (6)
H5	0.2117	0.7103	0.1876	0.031*
C6	0.3540 (2)	0.7641 (2)	0.21113 (15)	0.0332 (6)
H6A	0.4256	0.7438	0.2041	0.04*
H6B	0.3393	0.7553	0.2545	0.04*
C7	0.3407 (3)	0.8792 (3)	0.19396 (17)	0.0384 (7)
H7A	0.3387	0.9204	0.2313	0.046*
H7B	0.4005	0.9015	0.1703	0.046*
C8	0.2417 (2)	0.9002 (2)	0.15664 (15)	0.0309 (6)
H8	0.182	0.8755	0.1805	0.037*
C9	0.2483 (2)	0.8366 (2)	0.09816 (14)	0.0307 (6)
C10	0.2833 (2)	0.7217 (2)	0.10447 (13)	0.0261 (6)
C11	0.2242 (3)	0.8779 (3)	0.04395 (17)	0.0439 (8)
H11	0.2322	0.8361	0.0094	0.053*
C12	0.1851 (4)	0.9870 (3)	0.03404 (18)	0.0535 (10)
H12A	0.1287	0.9856	0.0045	0.064*
H12B	0.2406	1.0289	0.0169	0.064*
C13	0.1463 (3)	1.0377 (3)	0.09429 (18)	0.0481 (9)
C14	0.2265 (3)	1.0152 (3)	0.14356 (18)	0.0436 (8)
H14A	0.2055	1.0496	0.1812	0.052*
H14B	0.2925	1.0447	0.131	0.052*
C15	0.1282 (5)	1.1516 (4)	0.0829 (2)	0.0853 (19)
H15	0.0933	1.1636	0.0461	0.102*
C16	0.1472 (8)	1.2286 (4)	0.1089 (3)	0.123 (3)
H16A	0.182	1.2263	0.1463	0.147*
H16B	0.1275	1.2921	0.0922	0.147*
C17	0.0409 (3)	0.9895 (4)	0.1120 (2)	0.0610 (12)
H17A	0.0484	0.9156	0.1159	0.092*
H17B	−0.0093	1.0047	0.0806	0.092*
H17C	0.018	1.0181	0.1504	0.092*
C18	0.2726 (3)	0.5543 (3)	0.25738 (17)	0.0429 (8)
H18A	0.2051	0.5811	0.2676	0.064*
H18B	0.3243	0.5888	0.2817	0.064*
H18C	0.2745	0.481	0.2656	0.064*
C19	0.4032 (2)	0.5295 (2)	0.17572 (14)	0.0312 (6)
C20	0.3915 (2)	0.7082 (2)	0.07483 (14)	0.0332 (7)
H20A	0.3909	0.7371	0.0342	0.05*
H20B	0.4083	0.6356	0.0726	0.05*
H20C	0.4427	0.7434	0.0993	0.05*
O1	0.42045 (17)	0.46242 (17)	0.13726 (11)	0.0352 (5)
O2	0.47604 (18)	0.5668 (2)	0.21170 (12)	0.0437 (6)
H2	0.532	0.5404	0.2027	0.066*
C1'	0.8991 (3)	0.6408 (3)	0.09529 (17)	0.0415 (8)
H1'1	0.9703	0.6216	0.086	0.05*
H1'2	0.8959	0.716	0.0969	0.05*
C2'	0.8713 (3)	0.5981 (3)	0.15830 (16)	0.0468 (9)
H2'1	0.9222	0.6216	0.1881	0.056*
H2'2	0.8039	0.6248	0.1706	0.056*
C3'	0.8682 (3)	0.4805 (3)	0.15808 (16)	0.0429 (8)
H3'1	0.8463	0.4564	0.1983	0.051*
H3'2	0.9377	0.4542	0.1507	0.051*
C4'	0.7945 (2)	0.4360 (2)	0.10933 (15)	0.0322 (6)
C5'	0.8256 (2)	0.4816 (2)	0.04527 (14)	0.0271 (6)
H5'	0.8981	0.4603	0.0397	0.033*
C6'	0.7679 (2)	0.4328 (2)	−0.00971 (15)	0.0316 (6)
H6'1	0.7876	0.3603	−0.0131	0.038*
H6'2	0.6937	0.4357	−0.0021	0.038*
C7'	0.7919 (2)	0.4880 (2)	−0.07080 (14)	0.0299 (6)
H7'1	0.7984	0.4365	−0.1031	0.036*
H7'2	0.7342	0.5333	−0.0813	0.036*
C8'	0.8922 (2)	0.5526 (2)	−0.06797 (13)	0.0257 (6)
H8'	0.9494	0.5068	−0.0557	0.031*
C9'	0.8790 (2)	0.6354 (2)	−0.01921 (15)	0.0301 (6)
C10'	0.8288 (2)	0.6029 (2)	0.04225 (14)	0.0285 (6)
C11'	0.9096 (3)	0.7328 (2)	−0.02861 (17)	0.0402 (8)
H11'	0.8987	0.7801	0.003	0.048*
C12'	0.9605 (3)	0.7729 (3)	−0.08629 (19)	0.0435 (8)
H12C	1.018	0.8177	−0.0751	0.052*
H12D	0.9106	0.8144	−0.109	0.052*
C13'	1.0012 (2)	0.6844 (3)	−0.12842 (16)	0.0355 (7)
C14'	0.9179 (2)	0.5993 (2)	−0.13061 (14)	0.0332 (6)
H14C	0.8549	0.6283	−0.1481	0.04*
H14D	0.9414	0.5442	−0.1576	0.04*
C15'	1.0229 (3)	0.7320 (3)	−0.1906 (2)	0.0536 (10)
H15'	1.0743	0.7829	−0.1908	0.064*
C16'	0.9827 (4)	0.7138 (5)	−0.2418 (2)	0.0762 (15)
H16C	0.9307	0.664	−0.2453	0.091*
H16D	1.0047	0.7502	−0.2763	0.091*
C17'	1.1037 (2)	0.6415 (3)	−0.10289 (17)	0.0401 (8)
H17D	1.1267	0.5847	−0.128	0.06*
H17E	1.0932	0.6176	−0.0616	0.06*
H17F	1.1553	0.6954	−0.1031	0.06*
C18'	0.8066 (3)	0.3167 (3)	0.10861 (19)	0.0447 (8)
H18D	0.7936	0.2897	0.149	0.067*
H18E	0.876	0.2989	0.0963	0.067*
H18F	0.7579	0.2872	0.0801	0.067*
C19'	0.6819 (2)	0.4561 (2)	0.12987 (15)	0.0318 (6)
C20'	0.7191 (2)	0.6510 (2)	0.04652 (16)	0.0338 (7)
H20D	0.723	0.7242	0.0383	0.051*
H20E	0.6916	0.6401	0.087	0.051*
H20F	0.6743	0.6185	0.0169	0.051*
O1'	0.66053 (17)	0.4932 (2)	0.17988 (11)	0.0402 (5)
O2'	0.61042 (16)	0.42401 (18)	0.09132 (11)	0.0362 (5)
H2'	0.5527	0.4336	0.1063	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0352 (16)	0.0399 (17)	0.0356 (17)	0.0035 (13)	−0.0104 (13)	−0.0085 (13)
C2	0.0300 (15)	0.0364 (17)	0.052 (2)	−0.0012 (13)	−0.0083 (14)	−0.0164 (15)
C3	0.0293 (15)	0.0311 (15)	0.056 (2)	−0.0040 (12)	0.0048 (14)	−0.0024 (15)
C4	0.0268 (13)	0.0308 (14)	0.0273 (14)	0.0015 (11)	0.0060 (11)	0.0024 (11)
C5	0.0238 (12)	0.0294 (14)	0.0241 (14)	0.0008 (10)	0.0007 (10)	−0.0004 (11)
C6	0.0321 (15)	0.0382 (16)	0.0292 (15)	−0.0013 (12)	−0.0035 (12)	−0.0085 (13)
C7	0.0365 (16)	0.0379 (17)	0.0408 (19)	−0.0064 (13)	−0.0014 (14)	−0.0107 (14)
C8	0.0306 (14)	0.0302 (14)	0.0320 (15)	−0.0015 (11)	0.0090 (12)	−0.0022 (12)
C9	0.0304 (14)	0.0284 (14)	0.0333 (16)	0.0010 (11)	0.0095 (12)	0.0000 (12)
C10	0.0267 (13)	0.0283 (13)	0.0232 (14)	0.0010 (10)	0.0013 (10)	−0.0035 (11)
C11	0.056 (2)	0.0450 (19)	0.0308 (17)	0.0130 (16)	0.0074 (15)	0.0021 (14)
C12	0.070 (3)	0.050 (2)	0.041 (2)	0.0220 (19)	0.0139 (18)	0.0119 (17)
C13	0.064 (2)	0.0360 (17)	0.044 (2)	0.0177 (16)	0.0181 (18)	0.0112 (15)
C14	0.054 (2)	0.0311 (16)	0.046 (2)	0.0001 (14)	0.0140 (16)	−0.0039 (14)
C15	0.152 (5)	0.046 (3)	0.057 (3)	0.037 (3)	0.043 (3)	0.019 (2)
C16	0.259 (10)	0.047 (3)	0.063 (4)	0.002 (4)	0.052 (5)	0.001 (3)
C17	0.049 (2)	0.066 (3)	0.068 (3)	0.019 (2)	0.007 (2)	0.017 (2)
C18	0.0443 (19)	0.0463 (19)	0.0381 (19)	0.0087 (15)	0.0151 (15)	0.0136 (15)
C19	0.0302 (14)	0.0334 (15)	0.0301 (16)	0.0031 (12)	0.0049 (12)	0.0063 (12)
C20	0.0337 (15)	0.0368 (16)	0.0290 (16)	0.0009 (12)	0.0090 (12)	−0.0002 (12)
O1	0.0297 (11)	0.0339 (11)	0.0420 (13)	0.0043 (9)	0.0057 (9)	−0.0020 (9)
O2	0.0306 (11)	0.0593 (16)	0.0413 (14)	0.0109 (11)	−0.0038 (10)	−0.0125 (12)
C1'	0.0365 (17)	0.0484 (19)	0.0395 (18)	−0.0164 (14)	0.0051 (14)	−0.0145 (15)
C2'	0.0376 (18)	0.070 (2)	0.0332 (18)	−0.0149 (17)	0.0003 (14)	−0.0156 (17)
C3'	0.0282 (15)	0.070 (2)	0.0309 (17)	−0.0012 (15)	0.0022 (13)	−0.0002 (16)
C4'	0.0258 (14)	0.0394 (16)	0.0312 (16)	0.0013 (12)	0.0038 (12)	0.0000 (12)
C5'	0.0217 (12)	0.0287 (13)	0.0309 (15)	−0.0003 (10)	0.0043 (11)	−0.0007 (11)
C6'	0.0336 (15)	0.0293 (14)	0.0319 (16)	−0.0072 (12)	0.0048 (12)	−0.0071 (12)
C7'	0.0295 (14)	0.0318 (14)	0.0284 (15)	−0.0045 (11)	−0.0005 (11)	−0.0061 (12)
C8'	0.0259 (13)	0.0252 (13)	0.0261 (14)	0.0008 (10)	0.0033 (11)	−0.0027 (11)
C9'	0.0251 (13)	0.0291 (14)	0.0363 (16)	−0.0030 (11)	0.0088 (12)	−0.0072 (12)
C10'	0.0255 (13)	0.0261 (13)	0.0337 (16)	−0.0048 (10)	0.0063 (11)	−0.0087 (11)
C11'	0.0442 (18)	0.0266 (15)	0.050 (2)	−0.0019 (13)	0.0177 (15)	−0.0090 (14)
C12'	0.0411 (18)	0.0291 (16)	0.060 (2)	−0.0036 (13)	0.0171 (16)	0.0034 (15)
C13'	0.0319 (15)	0.0380 (16)	0.0366 (17)	−0.0001 (12)	0.0098 (13)	0.0089 (13)
C14'	0.0330 (15)	0.0371 (16)	0.0296 (15)	0.0026 (12)	0.0022 (12)	0.0000 (12)
C15'	0.045 (2)	0.063 (2)	0.053 (3)	0.0037 (17)	0.0147 (18)	0.022 (2)
C16'	0.079 (3)	0.111 (4)	0.039 (3)	0.004 (3)	0.008 (2)	0.013 (2)
C17'	0.0322 (16)	0.0484 (19)	0.0398 (19)	−0.0012 (13)	0.0072 (14)	0.0047 (15)
C18'	0.0447 (19)	0.0415 (18)	0.048 (2)	0.0055 (15)	0.0097 (16)	0.0135 (16)
C19'	0.0259 (14)	0.0368 (16)	0.0328 (16)	−0.0006 (11)	0.0042 (12)	0.0027 (12)
C20'	0.0332 (15)	0.0296 (14)	0.0387 (17)	0.0017 (12)	0.0126 (13)	−0.0055 (13)
O1'	0.0287 (11)	0.0606 (15)	0.0312 (12)	0.0039 (10)	0.0038 (9)	−0.0057 (11)
O2'	0.0251 (10)	0.0459 (13)	0.0374 (12)	−0.0053 (9)	0.0070 (9)	−0.0049 (10)

Geometric parameters (Å, º) top

C1—C2	1.542 (5)	C1'—C2'	1.520 (5)
C1—C10	1.548 (4)	C1'—C10'	1.545 (4)
C1—H1A	0.97	C1'—H1'1	0.97
C1—H1B	0.97	C1'—H1'2	0.97
C2—C3	1.511 (6)	C2'—C3'	1.514 (6)
C2—H2A	0.97	C2'—H2'1	0.97
C2—H2B	0.97	C2'—H2'2	0.97
C3—C4	1.540 (4)	C3'—C4'	1.534 (5)
C3—H3A	0.97	C3'—H3'1	0.97
C3—H3B	0.97	C3'—H3'2	0.97
C4—C19	1.534 (4)	C4'—C19'	1.538 (4)
C4—C18	1.543 (4)	C4'—C18'	1.544 (5)
C4—C5	1.577 (4)	C4'—C5'	1.565 (4)
C5—C6	1.539 (4)	C5'—C6'	1.542 (4)
C5—C10	1.553 (4)	C5'—C10'	1.563 (4)
C5—H5	0.98	C5'—H5'	0.98
C6—C7	1.537 (5)	C6'—C7'	1.539 (4)
C6—H6A	0.97	C6'—H6'1	0.97
C6—H6B	0.97	C6'—H6'2	0.97
C7—C8	1.535 (5)	C7'—C8'	1.536 (4)
C7—H7A	0.97	C7'—H7'1	0.97
C7—H7B	0.97	C7'—H7'2	0.97
C8—C9	1.515 (4)	C8'—C9'	1.514 (4)
C8—C14	1.520 (4)	C8'—C14'	1.526 (4)
C8—H8	0.98	C8'—H8'	0.98
C9—C11	1.331 (5)	C9'—C11'	1.329 (4)
C9—C10	1.552 (4)	C9'—C10'	1.544 (4)
C10—C20	1.545 (4)	C10'—C20'	1.545 (4)
C11—C12	1.507 (5)	C11'—C12'	1.507 (5)
C11—H11	0.93	C11'—H11'	0.93
C12—C13	1.548 (5)	C12'—C13'	1.553 (5)
C12—H12A	0.97	C12'—H12C	0.97
C12—H12B	0.97	C12'—H12D	0.97
C13—C15	1.505 (5)	C13'—C15'	1.511 (5)
C13—C14	1.516 (6)	C13'—C17'	1.534 (5)
C13—C17	1.540 (6)	C13'—C14'	1.534 (5)
C14—H14A	0.97	C14'—H14C	0.97
C14—H14B	0.97	C14'—H14D	0.97
C15—C16	1.167 (8)	C15'—C16'	1.251 (7)
C15—H15	0.93	C15'—H15'	0.93
C16—H16A	0.93	C16'—H16C	0.93
C16—H16B	0.93	C16'—H16D	0.93
C17—H17A	0.96	C17'—H17D	0.96
C17—H17B	0.96	C17'—H17E	0.96
C17—H17C	0.96	C17'—H17F	0.96
C18—H18A	0.96	C18'—H18D	0.96
C18—H18B	0.96	C18'—H18E	0.96
C18—H18C	0.96	C18'—H18F	0.96
C19—O1	1.223 (4)	C19'—O1'	1.220 (4)
C19—O2	1.313 (4)	C19'—O2'	1.312 (4)
C20—H20A	0.96	C20'—H20D	0.96
C20—H20B	0.96	C20'—H20E	0.96
C20—H20C	0.96	C20'—H20F	0.96
O2—H2	0.82	O2'—H2'	0.82

C2—C1—C10	113.6 (3)	C2'—C1'—C10'	115.0 (3)
C2—C1—H1A	108.9	C2'—C1'—H1'1	108.5
C10—C1—H1A	108.9	C10'—C1'—H1'1	108.5
C2—C1—H1B	108.9	C2'—C1'—H1'2	108.5
C10—C1—H1B	108.9	C10'—C1'—H1'2	108.5
H1A—C1—H1B	107.7	H1'1—C1'—H1'2	107.5
C3—C2—C1	111.5 (3)	C3'—C2'—C1'	111.4 (3)
C3—C2—H2A	109.3	C3'—C2'—H2'1	109.4
C1—C2—H2A	109.3	C1'—C2'—H2'1	109.4
C3—C2—H2B	109.3	C3'—C2'—H2'2	109.4
C1—C2—H2B	109.3	C1'—C2'—H2'2	109.4
H2A—C2—H2B	108	H2'1—C2'—H2'2	108
C2—C3—C4	114.2 (3)	C2'—C3'—C4'	113.1 (3)
C2—C3—H3A	108.7	C2'—C3'—H3'1	109
C4—C3—H3A	108.7	C4'—C3'—H3'1	109
C2—C3—H3B	108.7	C2'—C3'—H3'2	109
C4—C3—H3B	108.7	C4'—C3'—H3'2	109
H3A—C3—H3B	107.6	H3'1—C3'—H3'2	107.8
C19—C4—C3	109.8 (3)	C3'—C4'—C19'	108.6 (3)
C19—C4—C18	106.6 (2)	C3'—C4'—C18'	108.4 (3)
C3—C4—C18	107.9 (3)	C19'—C4'—C18'	105.4 (3)
C19—C4—C5	114.6 (2)	C3'—C4'—C5'	108.6 (2)
C3—C4—C5	108.1 (2)	C19'—C4'—C5'	115.9 (3)
C18—C4—C5	109.7 (2)	C18'—C4'—C5'	109.8 (3)
C6—C5—C10	111.3 (2)	C6'—C5'—C10'	112.8 (2)
C6—C5—C4	114.2 (2)	C6'—C5'—C4'	114.6 (2)
C10—C5—C4	115.6 (2)	C10'—C5'—C4'	114.8 (2)
C6—C5—H5	104.8	C6'—C5'—H5'	104.4
C10—C5—H5	104.8	C10'—C5'—H5'	104.4
C4—C5—H5	104.8	C4'—C5'—H5'	104.4
C5—C6—C7	112.3 (2)	C7'—C6'—C5'	112.7 (2)
C5—C6—H6A	109.1	C7'—C6'—H6'1	109
C7—C6—H6A	109.1	C5'—C6'—H6'1	109
C5—C6—H6B	109.1	C7'—C6'—H6'2	109
C7—C6—H6B	109.1	C5'—C6'—H6'2	109
H6A—C6—H6B	107.9	H6'1—C6'—H6'2	107.8
C8—C7—C6	113.0 (2)	C8'—C7'—C6'	112.5 (2)
C8—C7—H7A	109	C8'—C7'—H7'1	109.1
C6—C7—H7A	109	C6'—C7'—H7'1	109.1
C8—C7—H7B	109	C8'—C7'—H7'2	109.1
C6—C7—H7B	109	C6'—C7'—H7'2	109.1
H7A—C7—H7B	107.8	H7'1—C7'—H7'2	107.8
C9—C8—C14	112.0 (3)	C9'—C8'—C14'	111.9 (2)
C9—C8—C7	107.7 (3)	C9'—C8'—C7'	108.4 (2)
C14—C8—C7	112.1 (3)	C14'—C8'—C7'	111.1 (2)
C9—C8—H8	108.3	C9'—C8'—H8'	108.5
C14—C8—H8	108.3	C14'—C8'—H8'	108.5
C7—C8—H8	108.3	C7'—C8'—H8'	108.5
C11—C9—C8	121.1 (3)	C11'—C9'—C8'	121.5 (3)
C11—C9—C10	121.8 (3)	C11'—C9'—C10'	120.9 (3)
C8—C9—C10	117.1 (3)	C8'—C9'—C10'	117.6 (2)
C20—C10—C1	110.3 (3)	C20'—C10'—C9'	109.0 (3)
C20—C10—C9	109.4 (2)	C20'—C10'—C1'	111.3 (2)
C1—C10—C9	107.5 (2)	C9'—C10'—C1'	108.5 (2)
C20—C10—C5	112.8 (2)	C20'—C10'—C5'	111.9 (2)
C1—C10—C5	108.5 (2)	C9'—C10'—C5'	108.6 (2)
C9—C10—C5	108.1 (2)	C1'—C10'—C5'	107.4 (3)
C9—C11—C12	125.2 (3)	C9'—C11'—C12'	125.5 (3)
C9—C11—H11	117.4	C9'—C11'—H11'	117.3
C12—C11—H11	117.4	C12'—C11'—H11'	117.3
C11—C12—C13	112.3 (3)	C11'—C12'—C13'	112.8 (3)
C11—C12—H12A	109.1	C11'—C12'—H12C	109
C13—C12—H12A	109.1	C13'—C12'—H12C	109
C11—C12—H12B	109.1	C11'—C12'—H12D	109
C13—C12—H12B	109.1	C13'—C12'—H12D	109
H12A—C12—H12B	107.9	H12C—C12'—H12D	107.8
C15—C13—C14	114.1 (4)	C15'—C13'—C17'	108.1 (3)
C15—C13—C17	107.3 (4)	C15'—C13'—C14'	113.0 (3)
C14—C13—C17	110.2 (3)	C17'—C13'—C14'	110.8 (3)
C15—C13—C12	108.7 (3)	C15'—C13'—C12'	107.1 (3)
C14—C13—C12	107.4 (3)	C17'—C13'—C12'	109.9 (3)
C17—C13—C12	109.0 (4)	C14'—C13'—C12'	107.8 (3)
C13—C14—C8	114.0 (3)	C8'—C14'—C13'	113.9 (3)
C13—C14—H14A	108.8	C8'—C14'—H14C	108.8
C8—C14—H14A	108.8	C13'—C14'—H14C	108.8
C13—C14—H14B	108.8	C8'—C14'—H14D	108.8
C8—C14—H14B	108.8	C13'—C14'—H14D	108.8
H14A—C14—H14B	107.7	H14C—C14'—H14D	107.7
C16—C15—C13	135.5 (7)	C16'—C15'—C13'	130.2 (4)
C16—C15—H15	112.2	C16'—C15'—H15'	114.9
C13—C15—H15	112.2	C13'—C15'—H15'	114.9
C15—C16—H16A	120	C15'—C16'—H16C	120
C15—C16—H16B	120	C15'—C16'—H16D	120
H16A—C16—H16B	120	H16C—C16'—H16D	120
C13—C17—H17A	109.5	C13'—C17'—H17D	109.5
C13—C17—H17B	109.5	C13'—C17'—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17'—H17E	109.5
C13—C17—H17C	109.5	C13'—C17'—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17'—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17'—H17F	109.5
C4—C18—H18A	109.5	C4'—C18'—H18D	109.5
C4—C18—H18B	109.5	C4'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
C4—C18—H18C	109.5	C4'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
O1—C19—O2	122.5 (3)	O1'—C19'—O2'	122.4 (3)
O1—C19—C4	123.5 (3)	O1'—C19'—C4'	122.5 (3)
O2—C19—C4	114.0 (3)	O2'—C19'—C4'	114.9 (3)
C10—C20—H20A	109.5	C10'—C20'—H20D	109.5
C10—C20—H20B	109.5	C10'—C20'—H20E	109.5
H20A—C20—H20B	109.5	H20D—C20'—H20E	109.5
C10—C20—H20C	109.5	C10'—C20'—H20F	109.5
H20A—C20—H20C	109.5	H20D—C20'—H20F	109.5
H20B—C20—H20C	109.5	H20E—C20'—H20F	109.5
C19—O2—H2	109.5	C19'—O2'—H2'	109.5

C10—C1—C2—C3	54.8 (4)	C10'—C1'—C2'—C3'	54.7 (4)
C1—C2—C3—C4	−55.4 (4)	C1'—C2'—C3'—C4'	−55.4 (4)
C2—C3—C4—C19	−72.7 (3)	C2'—C3'—C4'—C19'	−72.1 (3)
C2—C3—C4—C18	171.5 (3)	C2'—C3'—C4'—C18'	173.9 (3)
C2—C3—C4—C5	52.9 (3)	C2'—C3'—C4'—C5'	54.7 (3)
C19—C4—C5—C6	−61.0 (3)	C3'—C4'—C5'—C6'	172.2 (3)
C3—C4—C5—C6	176.2 (3)	C19'—C4'—C5'—C6'	−65.4 (3)
C18—C4—C5—C6	58.8 (3)	C18'—C4'—C5'—C6'	53.8 (3)
C19—C4—C5—C10	70.1 (3)	C3'—C4'—C5'—C10'	−55.0 (3)
C3—C4—C5—C10	−52.7 (3)	C19'—C4'—C5'—C10'	67.5 (3)
C18—C4—C5—C10	−170.1 (3)	C18'—C4'—C5'—C10'	−173.3 (3)
C10—C5—C6—C7	45.5 (3)	C10'—C5'—C6'—C7'	39.9 (3)
C4—C5—C6—C7	178.7 (2)	C4'—C5'—C6'—C7'	173.7 (2)
C5—C6—C7—C8	14.7 (4)	C5'—C6'—C7'—C8'	19.4 (4)
C6—C7—C8—C9	−59.8 (3)	C6'—C7'—C8'—C9'	−61.1 (3)
C6—C7—C8—C14	176.4 (3)	C6'—C7'—C8'—C14'	175.6 (2)
C14—C8—C9—C11	−11.1 (4)	C14'—C8'—C9'—C11'	−13.8 (4)
C7—C8—C9—C11	−134.9 (3)	C7'—C8'—C9'—C11'	−136.6 (3)
C14—C8—C9—C10	169.4 (3)	C14'—C8'—C9'—C10'	166.3 (3)
C7—C8—C9—C10	45.6 (3)	C7'—C8'—C9'—C10'	43.5 (3)
C2—C1—C10—C20	71.9 (4)	C11'—C9'—C10'—C20'	71.0 (4)
C2—C1—C10—C9	−169.0 (3)	C8'—C9'—C10'—C20'	−109.2 (3)
C2—C1—C10—C5	−52.2 (3)	C11'—C9'—C10'—C1'	−50.4 (4)
C11—C9—C10—C20	68.8 (4)	C8'—C9'—C10'—C1'	129.4 (3)
C8—C9—C10—C20	−111.7 (3)	C11'—C9'—C10'—C5'	−166.9 (3)
C11—C9—C10—C1	−51.0 (4)	C8'—C9'—C10'—C5'	13.0 (3)
C8—C9—C10—C1	128.5 (3)	C2'—C1'—C10'—C20'	70.8 (4)
C11—C9—C10—C5	−168.0 (3)	C2'—C1'—C10'—C9'	−169.3 (3)
C8—C9—C10—C5	11.6 (3)	C2'—C1'—C10'—C5'	−52.1 (4)
C6—C5—C10—C20	62.5 (3)	C6'—C5'—C10'—C20'	64.1 (3)
C4—C5—C10—C20	−70.0 (3)	C4'—C5'—C10'—C20'	−69.6 (3)
C6—C5—C10—C1	−174.9 (2)	C6'—C5'—C10'—C9'	−56.3 (3)
C4—C5—C10—C1	52.6 (3)	C4'—C5'—C10'—C9'	170.0 (2)
C6—C5—C10—C9	−58.7 (3)	C6'—C5'—C10'—C1'	−173.5 (2)
C4—C5—C10—C9	168.9 (2)	C4'—C5'—C10'—C1'	52.8 (3)
C8—C9—C11—C12	−2.4 (6)	C8'—C9'—C11'—C12'	−0.6 (6)
C10—C9—C11—C12	177.1 (3)	C10'—C9'—C11'—C12'	179.2 (3)
C9—C11—C12—C13	−16.0 (6)	C9'—C11'—C12'—C13'	−15.2 (5)
C11—C12—C13—C15	169.3 (4)	C11'—C12'—C13'—C15'	165.0 (3)
C11—C12—C13—C14	45.4 (5)	C11'—C12'—C13'—C17'	−77.8 (4)
C11—C12—C13—C17	−74.0 (4)	C11'—C12'—C13'—C14'	43.1 (4)
C15—C13—C14—C8	177.8 (3)	C9'—C8'—C14'—C13'	45.2 (3)
C17—C13—C14—C8	57.1 (4)	C7'—C8'—C14'—C13'	166.5 (3)
C12—C13—C14—C8	−61.6 (4)	C15'—C13'—C14'—C8'	−178.1 (3)
C9—C8—C14—C13	44.4 (4)	C17'—C13'—C14'—C8'	60.3 (4)
C7—C8—C14—C13	165.6 (3)	C12'—C13'—C14'—C8'	−60.0 (4)
C14—C13—C15—C16	−15.6 (10)	C17'—C13'—C15'—C16'	124.4 (5)
C17—C13—C15—C16	106.8 (9)	C14'—C13'—C15'—C16'	1.3 (6)
C12—C13—C15—C16	−135.4 (8)	C12'—C13'—C15'—C16'	−117.2 (5)
C3—C4—C19—O1	5.7 (4)	C3'—C4'—C19'—O1'	−6.0 (4)
C18—C4—C19—O1	122.2 (3)	C18'—C4'—C19'—O1'	110.0 (4)
C5—C4—C19—O1	−116.2 (3)	C5'—C4'—C19'—O1'	−128.4 (3)
C3—C4—C19—O2	−171.4 (3)	C3'—C4'—C19'—O2'	178.4 (3)
C18—C4—C19—O2	−54.8 (3)	C18'—C4'—C19'—O2'	−65.6 (3)
C5—C4—C19—O2	66.8 (3)	C5'—C4'—C19'—O2'	55.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2′—H2′···O1	0.82	1.87	2.687 (3)	177
O2—H2···O1′	0.82	1.83	2.649 (3)	175

Experimental details

Crystal data
Chemical formula	C₂₀H₃₀O₂
M_r	302.44
Crystal system, space group	Tetragonal, P4₃
Temperature (K)	100
a, c (Å)	12.8697 (16), 21.768 (2)
V (Å³)	3605.5 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.20 × 0.02

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21616, 4824, 3830
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.709

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.158, 1.02
No. of reflections	4824
No. of parameters	405
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.29

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2'—H2'···O1	0.82	1.87	2.687 (3)	177
O2—H2···O1'	0.82	1.83	2.649 (3)	175

Acknowledgements

This research was supported by a grant under the program Strategic Scholarships for Frontier Research Network for the PhD Program Thai Doctoral degree from the Office of the Higher Education Commission, Thailand, the 90^th Anniversary of Chulalongkorn University Fund (Ratchadaphiseksomphot Endowment Fund), the Department of Chemistry, Faculty of Science, Chulalongkorn University, and the National Center of Excellence for Petroleum, Petrochemicals, and Advanced materials are also gratefully acknowledged. Finally, we thank the Research Funds from the Faculty of Science (A1B1), the Thai Government Stimulus Package 2 (TKK2555) under the Project for Establishment of Comprehensive Center for Innovative Food, Health Products and Agriculture for their support of X-ray crystallography analysis by supporting the X-ray analysis fund.

References

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Volume 66| Part 7| July 2010| Page o1531

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