(3S,3aS,5aS,7S,8S,10aS,10bR)-7,8-Dihydr­oxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-deca­hydro­cyclo­hepta­[e]indene-3a(1H)-carboxylic acid

Brito, I.; Bórquez, J.; Loyola, L.A.; Cárdenas, A.; López-Rodríguez, M.

doi:10.1107/S1600536808018941

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages o1348-o1349

doi:10.1107/S1600536808018941

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(3S,3aS,5aS,7S,8S,10aS,10bR)-7,8-Dihydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylic acid

Iván Brito,^a ^* Jorge Bórquez,^a Luis Alberto Loyola,^a Alejandro Cárdenas ^b and Matías López-Rodríguez ^c

^aDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, ^bDepartamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, and ^cInstituto de Bio-Orgánica 'Antonio González', Universidad de La Laguna, Astrofísico Francisco Sánchez N°2, La Laguna, Tenerife, Spain
^*Correspondence e-mail: ivanbritob@yahoo.com

(Received 20 June 2008; accepted 23 June 2008; online 28 June 2008)

The molecule of the title compound, C₂₀H₃₂O₄, is built up from three fused five-membered, six-membered and seven-membered rings. The five-membered ring has an envelope conformation, whereas the six- and seven-membered rings have chair conformations. The crystal structure is stabilized by strong intermolecular O—H⋯O hydrogen bonds, forming a three-dimensional network. The absolute configuration was assigned on the basis of earlier chemical studies.

Related literature

For related literature, see: Araya et al. (2003 ); Cremer & Pople (1975 ); Fuentes et al. (2005 ); Loyola et al. (1996 , 2004 ); Wickens (1995 ).

Experimental

Crystal data

C₂₀H₃₂O₄
M_r = 336.46
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.094 (7) Å
b = 12.728 (10) Å
c = 13.8776 (11) Å
V = 1959.6 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: none
9149 measured reflections
1922 independent reflections
1836 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.117
S = 1.13
1922 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.82	1.80	2.613 (3)	170
O3—H3⋯O2ⁱⁱ	0.82	2.01	2.825 (3)	173
O4—H4⋯O3ⁱⁱⁱ	0.82	1.94	2.752 (3)	172
C1—H1B⋯O2	0.97	2.44	2.889 (4)	108
C5—H5B⋯O1	0.97	2.51	3.054 (4)	116
C6—H6B⋯O4	0.97	2.52	2.901 (3)	104
C16—H16A⋯O3	0.96	2.46	2.809 (4)	101
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+2]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018941/bt2730sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018941/bt2730Isup2.hkl

checkCIF report

Comment top

Azorella compacta is a compact resinous cushion shrub that grows in the Andes of Peru, Bolivia, Argentina and Chile and has been used in folk medicine. The common name llareta is used for several species of the genus Azorella (Wickens, 1995). Mulinane diterpenes exhibits antiplasmodial (Loyola et al., 2004), anti-Tripanosoma cruzi (Araya et al., 2003) and antihyperglycemic (Fuentes et al., 2005) activities.We have undertaken the X-ray crystal-structure determination of the title compound in order to establish its molecular conformation and relative stereochemistry. We are not able to determine the absolute stereochemistry by X-ray methods and the configuration shown here was chosen to be in accord with that reported in previous chemical studies (Loyola et al., 1996). The structure consists of a mulinic acid skeleton and the isopropyl, methyl groups and carboxylic acid at C3, C5a, C8 and C3b are α-oriented respectively, whereas the hydroxyl groups at C8 and C7 are β-oriented. The cyclopentane (A), cyclohexane (B) and cycloheptene (C) rings are in an envelope, chair and chair conformation respectively [Q₂= 0.435 (2) Å, ϕ₂= 118.7 (3)° for rig A; Q_T= 0.581 (2) Å, θ = 174.4 (2)°, ϕ=131 (2)° for ring B; Q_T= 0.634 (2) Å, ϕ₂=78.4 (6)°, for ring C] (Cremer & Pople, 1975). The A and B and B and C rings are trans and cis-fused respectively. The molecular conformation is stabilized by four intramolecular hydrogen bonds and the crystal structure is stabilized by three intermolecular hydrogen bonds (Table 1).

Related literature top

For related literature, see: Araya et al. (2003); Cremer & Pople (1975); Fuentes et al. (2005); Loyola et al. (1996, 2004); Wickens (1995).

Experimental top

Dried and finely powdered whole plant of Azorella compacta (3,0 kg) were extracted with petroleum ether at room temperature. After filtration, the solvent was evaporated in vacuum yielding a gum (220 g). The concentrated petrol ether extract was adsorbed on silica gel (300 g) and slurried onto the top of a column containing silica gel (2.0 kg) in petroleum ether, and eluted with a petroleum ether/ethyl acetate gradient with increasing amounts of ethyl acetate to produce six fractions. Fraction 2 (100 g) eluted with petroleum ether/ethyl acetate(18:2) was further separated and purified by silica gel column chromatography(petroleum ether/ethyl acetate), 19:1) to give 600 mg of the title compound. The structure were elucidated by analysis of their spectroscopic data. Recrystallization from hexane-ethyl acetate (7:3) at room temperature afforded colourless crystals suitable for X-ray diffraction analysis.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecule of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

(3S,3aS,5aS,7S,8S,10aS,10bR)-7,8-Dihydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylic acid top

Crystal data top

C₂₀H₃₂O₄	F(000) = 736
M_r = 336.46	D_x = 1.14 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5686 reflections
a = 11.094 (7) Å	θ = 2.3–25.2°
b = 12.728 (10) Å	µ = 0.08 mm⁻¹
c = 13.8776 (11) Å	T = 298 K
V = 1959.6 (19) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	1836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.072
Graphite monochromator	θ_max = 25.2°, θ_min = 2.4°
ϕ scans, and ω scans with κ offsets	h = −9→13
9149 measured reflections	k = −11→15
1922 independent reflections	l = −15→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.039	w = 1/[σ²(F_o²) + (0.0775P)² + 0.1473P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.117	(Δ/σ)_max = 0.005
S = 1.13	Δρ_max = 0.21 e Å⁻³
1922 reflections	Δρ_min = −0.14 e Å⁻³
226 parameters

Crystal data top

C₂₀H₃₂O₄	V = 1959.6 (19) Å³
M_r = 336.46	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.094 (7) Å	µ = 0.08 mm⁻¹
b = 12.728 (10) Å	T = 298 K
c = 13.8776 (11) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	1836 reflections with I > 2σ(I)
9149 measured reflections	R_int = 0.072
1922 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.13	Δρ_max = 0.21 e Å⁻³
1922 reflections	Δρ_min = −0.14 e Å⁻³
226 parameters

Special details top

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	0.22790 (18)	0.80481 (16)	0.67764 (12)	0.0550 (5)
H1	0.2371	0.7969	0.6195	0.066 (2)*
O2	0.39658 (15)	0.89409 (15)	0.66282 (11)	0.0497 (5)
O3	0.01429 (13)	1.24195 (13)	1.01859 (10)	0.0361 (4)
H3	0.0408	1.1986	1.0568	0.066 (2)*
O4	0.27135 (13)	1.21546 (12)	0.99028 (10)	0.0352 (4)
H4	0.3422	1.2321	0.9835	0.066 (2)*
C1	0.44994 (19)	1.03680 (17)	0.81893 (16)	0.0368 (5)
H1A	0.4778	1.0971	0.8554	0.046 (2)*
H1B	0.4745	1.0446	0.7522	0.046 (2)*
C2	0.4986 (2)	0.93369 (19)	0.86208 (19)	0.0431 (6)
H2A	0.5396	0.9477	0.9224	0.046 (2)*
H2B	0.5554	0.9014	0.818	0.046 (2)*
C3	0.3898 (2)	0.85939 (16)	0.87930 (14)	0.0338 (5)
H3A	0.3642	0.8699	0.9462	0.041*
C3A	0.28837 (18)	0.90550 (15)	0.81408 (13)	0.0278 (4)
C4	0.15886 (19)	0.88598 (16)	0.84672 (15)	0.0330 (4)
H4A	0.1524	0.8994	0.9153	0.046 (2)*
H4B	0.1381	0.813	0.8355	0.046 (2)*
C5	0.0704 (2)	0.95643 (19)	0.79272 (17)	0.0407 (5)
H5A	−0.0097	0.9439	0.8182	0.046 (2)*
H5B	0.0698	0.9354	0.7255	0.046 (2)*
C5A	0.09599 (19)	1.07500 (17)	0.79757 (15)	0.0343 (5)
C6	0.06692 (18)	1.11212 (16)	0.90075 (14)	0.0329 (4)
H6A	−0.0136	1.0875	0.9159	0.046 (2)*
H6B	0.1217	1.0758	0.9438	0.046 (2)*
C7	0.07182 (19)	1.22815 (17)	0.92647 (14)	0.0322 (4)
H7	0.0232	1.2658	0.8787	0.039*
C8	0.1969 (2)	1.27901 (16)	0.92731 (15)	0.0332 (5)
C9	0.2535 (2)	1.28268 (17)	0.82860 (15)	0.0377 (5)
H9	0.2827	1.3481	0.8099	0.045*
C10	0.2678 (2)	1.20670 (18)	0.76493 (15)	0.0390 (5)
H10	0.3086	1.2265	0.7093	0.047*
C10A	0.22889 (19)	1.09300 (16)	0.76724 (13)	0.0319 (4)
H10A	0.2354	1.0675	0.7008	0.038*
C10B	0.31312 (18)	1.02422 (15)	0.82710 (13)	0.0286 (4)
H10B	0.2936	1.0397	0.8945	0.034*
C11	0.4236 (2)	0.74293 (17)	0.86931 (15)	0.0398 (5)
H11	0.4606	0.7335	0.8058	0.048*
C12	0.5173 (3)	0.7132 (3)	0.9447 (2)	0.0599 (8)
H12A	0.5844	0.7607	0.9408	0.066 (2)*
H12B	0.5448	0.6427	0.9331	0.066 (2)*
H12C	0.482	0.7173	1.0077	0.066 (2)*
C13	0.3176 (3)	0.6675 (2)	0.8759 (3)	0.0675 (9)
H13A	0.2766	0.6777	0.9362	0.066 (2)*
H13B	0.3463	0.5965	0.8721	0.066 (2)*
H13C	0.2628	0.6808	0.8238	0.066 (2)*
C14	0.31036 (18)	0.86941 (16)	0.71064 (13)	0.0301 (4)
C15	0.0128 (3)	1.1305 (2)	0.72577 (19)	0.0545 (7)
H15A	0.0256	1.1022	0.6625	0.066 (2)*
H15B	0.0303	1.2044	0.7254	0.066 (2)*
H15C	−0.0696	1.1198	0.7444	0.066 (2)*
C16	0.1909 (3)	1.39039 (18)	0.9685 (2)	0.0525 (6)
H16A	0.1586	1.388	1.0326	0.066 (2)*
H16B	0.1399	1.433	0.9285	0.066 (2)*
H16C	0.2704	1.42	0.9702	0.066 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0571 (10)	0.0727 (11)	0.0351 (9)	−0.0269 (10)	0.0080 (8)	−0.0216 (8)
O2	0.0426 (9)	0.0711 (12)	0.0353 (8)	−0.0131 (8)	0.0105 (7)	−0.0178 (8)
O3	0.0291 (7)	0.0475 (9)	0.0318 (8)	0.0110 (6)	0.0051 (6)	−0.0001 (6)
O4	0.0272 (7)	0.0449 (8)	0.0335 (7)	−0.0028 (7)	0.0012 (6)	0.0082 (6)
C1	0.0314 (11)	0.0364 (10)	0.0427 (11)	−0.0054 (9)	0.0010 (9)	−0.0081 (9)
C2	0.0300 (10)	0.0459 (12)	0.0534 (14)	0.0010 (10)	−0.0109 (10)	−0.0080 (10)
C3	0.0382 (11)	0.0376 (10)	0.0255 (9)	0.0046 (9)	−0.0058 (8)	−0.0040 (8)
C3A	0.0273 (9)	0.0316 (9)	0.0245 (9)	−0.0005 (8)	0.0013 (8)	−0.0027 (7)
C4	0.0304 (9)	0.0366 (10)	0.0320 (9)	−0.0052 (8)	0.0054 (8)	−0.0059 (8)
C5	0.0281 (10)	0.0482 (12)	0.0457 (12)	−0.0008 (9)	−0.0036 (9)	−0.0128 (10)
C5A	0.0308 (10)	0.0420 (11)	0.0302 (10)	0.0071 (9)	−0.0045 (8)	−0.0040 (8)
C6	0.0252 (9)	0.0400 (10)	0.0337 (10)	0.0016 (8)	0.0015 (8)	−0.0007 (8)
C7	0.0290 (9)	0.0411 (10)	0.0264 (9)	0.0112 (9)	0.0033 (8)	0.0017 (8)
C8	0.0369 (10)	0.0317 (9)	0.0310 (10)	0.0064 (9)	0.0034 (8)	0.0015 (8)
C9	0.0434 (12)	0.0321 (9)	0.0377 (11)	0.0021 (9)	0.0084 (9)	0.0100 (8)
C10	0.0462 (12)	0.0413 (11)	0.0294 (10)	0.0074 (10)	0.0113 (9)	0.0084 (8)
C10A	0.0372 (10)	0.0383 (10)	0.0201 (8)	0.0061 (9)	0.0026 (8)	−0.0012 (7)
C10B	0.0285 (10)	0.0310 (9)	0.0263 (9)	−0.0004 (8)	0.0019 (7)	−0.0029 (7)
C11	0.0444 (12)	0.0388 (11)	0.0362 (11)	0.0101 (10)	−0.0013 (10)	0.0028 (8)
C12	0.0706 (18)	0.0638 (16)	0.0454 (13)	0.0282 (15)	−0.0104 (13)	0.0082 (11)
C13	0.0611 (18)	0.0407 (13)	0.101 (2)	0.0003 (13)	0.0004 (17)	0.0144 (14)
C14	0.0301 (9)	0.0331 (9)	0.0272 (9)	0.0010 (8)	−0.0024 (8)	−0.0027 (7)
C15	0.0484 (13)	0.0693 (16)	0.0458 (13)	0.0188 (13)	−0.0178 (12)	−0.0044 (13)
C16	0.0619 (15)	0.0367 (12)	0.0588 (15)	−0.0006 (11)	0.0168 (13)	−0.0067 (11)

Geometric parameters (Å, º) top

O1—C14	1.312 (3)	C6—C7	1.520 (3)
O1—H1	0.82	C6—H6A	0.97
O2—C14	1.206 (3)	C6—H6B	0.97
O3—C7	1.440 (2)	C7—C8	1.531 (3)
O3—H3	0.82	C7—H7	0.98
O4—C8	1.449 (3)	C8—C9	1.508 (3)
O4—H4	0.82	C8—C16	1.530 (3)
C1—C10B	1.531 (3)	C9—C10	1.319 (3)
C1—C2	1.540 (3)	C9—H9	0.93
C1—H1A	0.97	C10—C10A	1.510 (3)
C1—H1B	0.97	C10—H10	0.93
C2—C3	1.551 (3)	C10A—C10B	1.526 (3)
C2—H2A	0.97	C10A—H10A	0.98
C2—H2B	0.97	C10B—H10B	0.98
C3—C11	1.535 (3)	C11—C12	1.523 (3)
C3—C3A	1.559 (3)	C11—C13	1.521 (4)
C3—H3A	0.98	C11—H11	0.98
C3A—C4	1.527 (3)	C12—H12A	0.96
C3A—C14	1.527 (3)	C12—H12B	0.96
C3A—C10B	1.546 (3)	C12—H12C	0.96
C4—C5	1.526 (3)	C13—H13A	0.96
C4—H4A	0.97	C13—H13B	0.96
C4—H4B	0.97	C13—H13C	0.96
C5—C5A	1.537 (3)	C15—H15A	0.96
C5—H5A	0.97	C15—H15B	0.96
C5—H5B	0.97	C15—H15C	0.96
C5A—C15	1.531 (3)	C16—H16A	0.96
C5A—C6	1.542 (3)	C16—H16B	0.96
C5A—C10A	1.550 (3)	C16—H16C	0.96

C14—O1—H1	109.5	O4—C8—C9	109.10 (16)
C7—O3—H3	109.5	O4—C8—C16	108.5 (2)
C8—O4—H4	109.5	C9—C8—C16	109.20 (18)
C10B—C1—C2	103.26 (18)	O4—C8—C7	106.57 (16)
C10B—C1—H1A	111.1	C9—C8—C7	112.58 (18)
C2—C1—H1A	111.1	C16—C8—C7	110.82 (19)
C10B—C1—H1B	111.1	C10—C9—C8	129.5 (2)
C2—C1—H1B	111.1	C10—C9—H9	115.3
H1A—C1—H1B	109.1	C8—C9—H9	115.3
C1—C2—C3	107.89 (18)	C9—C10—C10A	130.8 (2)
C1—C2—H2A	110.1	C9—C10—H10	114.6
C3—C2—H2A	110.1	C10A—C10—H10	114.6
C1—C2—H2B	110.1	C10—C10A—C10B	112.72 (18)
C3—C2—H2B	110.1	C10—C10A—C5A	114.76 (18)
H2A—C2—H2B	108.4	C10B—C10A—C5A	110.47 (16)
C11—C3—C2	112.66 (19)	C10—C10A—H10A	106.1
C11—C3—C3A	119.15 (17)	C10B—C10A—H10A	106.1
C2—C3—C3A	104.03 (17)	C5A—C10A—H10A	106.1
C11—C3—H3A	106.8	C10A—C10B—C1	120.45 (18)
C2—C3—H3A	106.8	C10A—C10B—C3A	112.84 (16)
C3A—C3—H3A	106.8	C1—C10B—C3A	105.65 (16)
C4—C3A—C14	112.35 (16)	C10A—C10B—H10B	105.6
C4—C3A—C10B	106.94 (16)	C1—C10B—H10B	105.6
C14—C3A—C10B	112.05 (16)	C3A—C10B—H10B	105.6
C4—C3A—C3	116.49 (17)	C12—C11—C13	109.3 (2)
C14—C3A—C3	108.49 (16)	C12—C11—C3	110.2 (2)
C10B—C3A—C3	99.89 (15)	C13—C11—C3	114.5 (2)
C3A—C4—C5	111.34 (17)	C12—C11—H11	107.5
C3A—C4—H4A	109.4	C13—C11—H11	107.5
C5—C4—H4A	109.4	C3—C11—H11	107.5
C3A—C4—H4B	109.4	C11—C12—H12A	109.5
C5—C4—H4B	109.4	C11—C12—H12B	109.5
H4A—C4—H4B	108	H12A—C12—H12B	109.5
C4—C5—C5A	115.89 (18)	C11—C12—H12C	109.5
C4—C5—H5A	108.3	H12A—C12—H12C	109.5
C5A—C5—H5A	108.3	H12B—C12—H12C	109.5
C4—C5—H5B	108.3	C11—C13—H13A	109.5
C5A—C5—H5B	108.3	C11—C13—H13B	109.5
H5A—C5—H5B	107.4	H13A—C13—H13B	109.5
C15—C5A—C5	108.27 (19)	C11—C13—H13C	109.5
C15—C5A—C6	109.69 (18)	H13A—C13—H13C	109.5
C5—C5A—C6	107.63 (18)	H13B—C13—H13C	109.5
C15—C5A—C10A	109.16 (19)	O2—C14—O1	121.61 (18)
C5—C5A—C10A	107.99 (17)	O2—C14—C3A	124.46 (18)
C6—C5A—C10A	113.94 (17)	O1—C14—C3A	113.90 (17)
C7—C6—C5A	120.54 (18)	C5A—C15—H15A	109.5
C7—C6—H6A	107.2	C5A—C15—H15B	109.5
C5A—C6—H6A	107.2	H15A—C15—H15B	109.5
C7—C6—H6B	107.2	C5A—C15—H15C	109.5
C5A—C6—H6B	107.2	H15A—C15—H15C	109.5
H6A—C6—H6B	106.8	H15B—C15—H15C	109.5
O3—C7—C6	108.13 (17)	C8—C16—H16A	109.5
O3—C7—C8	110.08 (17)	C8—C16—H16B	109.5
C6—C7—C8	116.42 (17)	H16A—C16—H16B	109.5
O3—C7—H7	107.3	C8—C16—H16C	109.5
C6—C7—H7	107.3	H16A—C16—H16C	109.5
C8—C7—H7	107.3	H16B—C16—H16C	109.5

C10B—C1—C2—C3	8.2 (2)	C9—C10—C10A—C10B	−79.8 (3)
C1—C2—C3—C11	149.26 (18)	C9—C10—C10A—C5A	47.8 (3)
C1—C2—C3—C3A	18.8 (2)	C15—C5A—C10A—C10	60.6 (2)
C11—C3—C3A—C4	81.3 (2)	C5—C5A—C10A—C10	178.06 (18)
C2—C3—C3A—C4	−152.25 (18)	C6—C5A—C10A—C10	−62.4 (2)
C11—C3—C3A—C14	−46.6 (2)	C15—C5A—C10A—C10B	−170.67 (17)
C2—C3—C3A—C14	79.8 (2)	C5—C5A—C10A—C10B	−53.2 (2)
C11—C3—C3A—C10B	−164.02 (18)	C6—C5A—C10A—C10B	66.3 (2)
C2—C3—C3A—C10B	−37.57 (19)	C10—C10A—C10B—C1	−43.1 (2)
C14—C3A—C4—C5	−68.2 (2)	C5A—C10A—C10B—C1	−172.95 (17)
C10B—C3A—C4—C5	55.2 (2)	C10—C10A—C10B—C3A	−169.03 (16)
C3—C3A—C4—C5	165.83 (16)	C5A—C10A—C10B—C3A	61.1 (2)
C3A—C4—C5—C5A	−55.1 (2)	C2—C1—C10B—C10A	−162.12 (17)
C4—C5—C5A—C15	170.12 (19)	C2—C1—C10B—C3A	−32.9 (2)
C4—C5—C5A—C6	−71.4 (2)	C4—C3A—C10B—C10A	−60.5 (2)
C4—C5—C5A—C10A	52.0 (2)	C14—C3A—C10B—C10A	63.1 (2)
C15—C5A—C6—C7	−56.7 (3)	C3—C3A—C10B—C10A	177.76 (15)
C5—C5A—C6—C7	−174.27 (18)	C4—C3A—C10B—C1	165.97 (16)
C10A—C5A—C6—C7	66.0 (2)	C14—C3A—C10B—C1	−70.5 (2)
C5A—C6—C7—O3	166.72 (16)	C3—C3A—C10B—C1	44.2 (2)
C5A—C6—C7—C8	−68.8 (2)	C2—C3—C11—C12	62.0 (3)
O3—C7—C8—O4	69.69 (19)	C3A—C3—C11—C12	−175.7 (2)
C6—C7—C8—O4	−53.8 (2)	C2—C3—C11—C13	−174.3 (2)
O3—C7—C8—C9	−170.74 (16)	C3A—C3—C11—C13	−52.1 (3)
C6—C7—C8—C9	65.8 (2)	C4—C3A—C14—O2	165.1 (2)
O3—C7—C8—C16	−48.1 (2)	C10B—C3A—C14—O2	44.7 (3)
C6—C7—C8—C16	−171.59 (18)	C3—C3A—C14—O2	−64.7 (3)
O4—C8—C9—C10	67.3 (3)	C4—C3A—C14—O1	−17.0 (2)
C16—C8—C9—C10	−174.3 (3)	C10B—C3A—C14—O1	−137.48 (19)
C7—C8—C9—C10	−50.8 (3)	C3—C3A—C14—O1	113.2 (2)
C8—C9—C10—C10A	2.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.80	2.613 (3)	170
O3—H3···O2ⁱⁱ	0.82	2.01	2.825 (3)	173
O4—H4···O3ⁱⁱⁱ	0.82	1.94	2.752 (3)	172
C1—H1B···O2	0.97	2.44	2.889 (4)	108
C5—H5B···O1	0.97	2.51	3.054 (4)	116
C6—H6B···O4	0.97	2.52	2.901 (3)	104
C16—H16A···O3	0.96	2.46	2.809 (4)	101

Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x+1/2, −y+2, z+1/2; (iii) x+1/2, −y+5/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₃₂O₄
M_r	336.46
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	11.094 (7), 12.728 (10), 13.8776 (11)
V (Å³)	1959.6 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9149, 1922, 1836
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.13
No. of reflections	1922
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.14

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	1.80	2.613 (3)	170
O3—H3···O2ⁱⁱ	0.82	2.01	2.825 (3)	173
O4—H4···O3ⁱⁱⁱ	0.82	1.94	2.752 (3)	172
C1—H1B···O2	0.97	2.44	2.889 (4)	108
C5—H5B···O1	0.97	2.51	3.054 (4)	116
C6—H6B···O4	0.97	2.52	2.901 (3)	104
C16—H16A···O3	0.96	2.46	2.809 (4)	101

Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x+1/2, −y+2, z+1/2; (iii) x+1/2, −y+5/2, −z+2.

Acknowledgements

LAL thanks the Fondo Nacional de Desarrollo Científico y Tecnológico de Chile for grant 1060339. We thank the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the Cambridge Structural Database.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Araya, J. E., Neira, I., Da Silva, S., Mortara, R. A., Manque, P., Cordero, E., Sagua, H., Loyola, A., Bórquez, J., Morales, G. & González, J. (2003). Mem. Inst. Oswaldo Cruz, Rio de Janeiro, 98, 413–418. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York; Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 64| Part 7| July 2008| Pages o1348-o1349

doi:10.1107/S1600536808018941

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3S,3aS,5aS,7S,8S,10aS,10bR)-7,8-Dihydr­­oxy-3-iso­propyl-5a,8-di­methyl-2,3,4,5,5a,6,7,8,10a,10b-deca­hydro­cyclo­hepta­[e]indene-3a(1H)-carboxylic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3S,3aS,5aS,7S,8S,10aS,10bR)-7,8-Dihydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylic acid