Literature DB >> 21202969

(3S,3aS,5aS,7S,8S,10aS,10bR)-7,8-Dihydr-oxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-deca-hydro-cyclo-hepta-[e]indene-3a(1H)-carboxylic acid.

Iván Brito, Jorge Bórquez, Luis Alberto Loyola, Alejandro Cárdenas, Matías López-Rodríguez.   

Abstract

The mol-ecule of the title compound, C(20)H(32)O(4), 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 inter-molecular O-H⋯O hydrogen bonds, forming a three-dimensional network. The absolute configuration was assigned on the basis of earlier chemical studies.

Entities:  

Year:  2008        PMID： 21202969      PMCID： PMC2961850          DOI： 10.1107/S1600536808018941

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 336.46 Orthorhombic, 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[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.117 S = 1.13 1922 reflections 226 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.14 e Å−3 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018941/bt2730sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018941/bt2730Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H32O4F000 = 736
Mr = 336.46Dx = 1.14 Mg m−3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5686 reflections
a = 11.094 (7) Åθ = 2.3–25.2º
b = 12.728 (10) ŵ = 0.08 mm−1
c = 13.8776 (11) ÅT = 298 (2) K
V = 1959.6 (19) Å3Block, colorless
Z = 40.30 × 0.20 × 0.10 mm
Nonius KappaCCD area-detector diffractometer1836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.072
Monochromator: graphiteθmax = 25.2º
φ scans, and ω scans with κ offsetsθmin = 2.4º
Absorption correction: noneh = −9→13
9149 measured reflectionsk = −11→15
1922 independent reflectionsl = −15→16
Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.0775P)2 + 0.1473P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.039(Δ/σ)max = 0.005
wR(F2) = 0.117Δρmax = 0.21 e Å−3
S = 1.13Δρmin = −0.14 e Å−3
1922 reflectionsExtinction correction: none
226 parameters
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.
xyzUiso*/Ueq
O10.22790 (18)0.80481 (16)0.67764 (12)0.0550 (5)
H10.23710.79690.61950.066 (2)*
O20.39658 (15)0.89409 (15)0.66282 (11)0.0497 (5)
O30.01429 (13)1.24195 (13)1.01859 (10)0.0361 (4)
H30.04081.19861.05680.066 (2)*
O40.27135 (13)1.21546 (12)0.99028 (10)0.0352 (4)
H40.34221.23210.98350.066 (2)*
C10.44994 (19)1.03680 (17)0.81893 (16)0.0368 (5)
H1A0.47781.09710.85540.046 (2)*
H1B0.47451.04460.75220.046 (2)*
C20.4986 (2)0.93369 (19)0.86208 (19)0.0431 (6)
H2A0.53960.94770.92240.046 (2)*
H2B0.55540.90140.8180.046 (2)*
C30.3898 (2)0.85939 (16)0.87930 (14)0.0338 (5)
H3A0.36420.86990.94620.041*
C3A0.28837 (18)0.90550 (15)0.81408 (13)0.0278 (4)
C40.15886 (19)0.88598 (16)0.84672 (15)0.0330 (4)
H4A0.15240.89940.91530.046 (2)*
H4B0.13810.8130.83550.046 (2)*
C50.0704 (2)0.95643 (19)0.79272 (17)0.0407 (5)
H5A−0.00970.94390.81820.046 (2)*
H5B0.06980.93540.72550.046 (2)*
C5A0.09599 (19)1.07500 (17)0.79757 (15)0.0343 (5)
C60.06692 (18)1.11212 (16)0.90075 (14)0.0329 (4)
H6A−0.01361.08750.91590.046 (2)*
H6B0.12171.07580.94380.046 (2)*
C70.07182 (19)1.22815 (17)0.92647 (14)0.0322 (4)
H70.02321.26580.87870.039*
C80.1969 (2)1.27901 (16)0.92731 (15)0.0332 (5)
C90.2535 (2)1.28268 (17)0.82860 (15)0.0377 (5)
H90.28271.34810.80990.045*
C100.2678 (2)1.20670 (18)0.76493 (15)0.0390 (5)
H100.30861.22650.70930.047*
C10A0.22889 (19)1.09300 (16)0.76724 (13)0.0319 (4)
H10A0.23541.06750.70080.038*
C10B0.31312 (18)1.02422 (15)0.82710 (13)0.0286 (4)
H10B0.29361.03970.89450.034*
C110.4236 (2)0.74293 (17)0.86931 (15)0.0398 (5)
H110.46060.73350.80580.048*
C120.5173 (3)0.7132 (3)0.9447 (2)0.0599 (8)
H12A0.58440.76070.94080.066 (2)*
H12B0.54480.64270.93310.066 (2)*
H12C0.4820.71731.00770.066 (2)*
C130.3176 (3)0.6675 (2)0.8759 (3)0.0675 (9)
H13A0.27660.67770.93620.066 (2)*
H13B0.34630.59650.87210.066 (2)*
H13C0.26280.68080.82380.066 (2)*
C140.31036 (18)0.86941 (16)0.71064 (13)0.0301 (4)
C150.0128 (3)1.1305 (2)0.72577 (19)0.0545 (7)
H15A0.02561.10220.66250.066 (2)*
H15B0.03031.20440.72540.066 (2)*
H15C−0.06961.11980.74440.066 (2)*
C160.1909 (3)1.39039 (18)0.9685 (2)0.0525 (6)
H16A0.15861.3881.03260.066 (2)*
H16B0.13991.4330.92850.066 (2)*
H16C0.27041.420.97020.066 (2)*
U11U22U33U12U13U23
O10.0571 (10)0.0727 (11)0.0351 (9)−0.0269 (10)0.0080 (8)−0.0216 (8)
O20.0426 (9)0.0711 (12)0.0353 (8)−0.0131 (8)0.0105 (7)−0.0178 (8)
O30.0291 (7)0.0475 (9)0.0318 (8)0.0110 (6)0.0051 (6)−0.0001 (6)
O40.0272 (7)0.0449 (8)0.0335 (7)−0.0028 (7)0.0012 (6)0.0082 (6)
C10.0314 (11)0.0364 (10)0.0427 (11)−0.0054 (9)0.0010 (9)−0.0081 (9)
C20.0300 (10)0.0459 (12)0.0534 (14)0.0010 (10)−0.0109 (10)−0.0080 (10)
C30.0382 (11)0.0376 (10)0.0255 (9)0.0046 (9)−0.0058 (8)−0.0040 (8)
C3A0.0273 (9)0.0316 (9)0.0245 (9)−0.0005 (8)0.0013 (8)−0.0027 (7)
C40.0304 (9)0.0366 (10)0.0320 (9)−0.0052 (8)0.0054 (8)−0.0059 (8)
C50.0281 (10)0.0482 (12)0.0457 (12)−0.0008 (9)−0.0036 (9)−0.0128 (10)
C5A0.0308 (10)0.0420 (11)0.0302 (10)0.0071 (9)−0.0045 (8)−0.0040 (8)
C60.0252 (9)0.0400 (10)0.0337 (10)0.0016 (8)0.0015 (8)−0.0007 (8)
C70.0290 (9)0.0411 (10)0.0264 (9)0.0112 (9)0.0033 (8)0.0017 (8)
C80.0369 (10)0.0317 (9)0.0310 (10)0.0064 (9)0.0034 (8)0.0015 (8)
C90.0434 (12)0.0321 (9)0.0377 (11)0.0021 (9)0.0084 (9)0.0100 (8)
C100.0462 (12)0.0413 (11)0.0294 (10)0.0074 (10)0.0113 (9)0.0084 (8)
C10A0.0372 (10)0.0383 (10)0.0201 (8)0.0061 (9)0.0026 (8)−0.0012 (7)
C10B0.0285 (10)0.0310 (9)0.0263 (9)−0.0004 (8)0.0019 (7)−0.0029 (7)
C110.0444 (12)0.0388 (11)0.0362 (11)0.0101 (10)−0.0013 (10)0.0028 (8)
C120.0706 (18)0.0638 (16)0.0454 (13)0.0282 (15)−0.0104 (13)0.0082 (11)
C130.0611 (18)0.0407 (13)0.101 (2)0.0003 (13)0.0004 (17)0.0144 (14)
C140.0301 (9)0.0331 (9)0.0272 (9)0.0010 (8)−0.0024 (8)−0.0027 (7)
C150.0484 (13)0.0693 (16)0.0458 (13)0.0188 (13)−0.0178 (12)−0.0044 (13)
C160.0619 (15)0.0367 (12)0.0588 (15)−0.0006 (11)0.0168 (13)−0.0067 (11)
O1—C141.312 (3)C6—C71.520 (3)
O1—H10.82C6—H6A0.97
O2—C141.206 (3)C6—H6B0.97
O3—C71.440 (2)C7—C81.531 (3)
O3—H30.82C7—H70.98
O4—C81.449 (3)C8—C91.508 (3)
O4—H40.82C8—C161.530 (3)
C1—C10B1.531 (3)C9—C101.319 (3)
C1—C21.540 (3)C9—H90.93
C1—H1A0.97C10—C10A1.510 (3)
C1—H1B0.97C10—H100.93
C2—C31.551 (3)C10A—C10B1.526 (3)
C2—H2A0.97C10A—H10A0.98
C2—H2B0.97C10B—H10B0.98
C3—C111.535 (3)C11—C121.523 (3)
C3—C3A1.559 (3)C11—C131.521 (4)
C3—H3A0.98C11—H110.98
C3A—C41.527 (3)C12—H12A0.96
C3A—C141.527 (3)C12—H12B0.96
C3A—C10B1.546 (3)C12—H12C0.96
C4—C51.526 (3)C13—H13A0.96
C4—H4A0.97C13—H13B0.96
C4—H4B0.97C13—H13C0.96
C5—C5A1.537 (3)C15—H15A0.96
C5—H5A0.97C15—H15B0.96
C5—H5B0.97C15—H15C0.96
C5A—C151.531 (3)C16—H16A0.96
C5A—C61.542 (3)C16—H16B0.96
C5A—C10A1.550 (3)C16—H16C0.96
C14—O1—H1109.5O4—C8—C9109.10 (16)
C7—O3—H3109.5O4—C8—C16108.5 (2)
C8—O4—H4109.5C9—C8—C16109.20 (18)
C10B—C1—C2103.26 (18)O4—C8—C7106.57 (16)
C10B—C1—H1A111.1C9—C8—C7112.58 (18)
C2—C1—H1A111.1C16—C8—C7110.82 (19)
C10B—C1—H1B111.1C10—C9—C8129.5 (2)
C2—C1—H1B111.1C10—C9—H9115.3
H1A—C1—H1B109.1C8—C9—H9115.3
C1—C2—C3107.89 (18)C9—C10—C10A130.8 (2)
C1—C2—H2A110.1C9—C10—H10114.6
C3—C2—H2A110.1C10A—C10—H10114.6
C1—C2—H2B110.1C10—C10A—C10B112.72 (18)
C3—C2—H2B110.1C10—C10A—C5A114.76 (18)
H2A—C2—H2B108.4C10B—C10A—C5A110.47 (16)
C11—C3—C2112.66 (19)C10—C10A—H10A106.1
C11—C3—C3A119.15 (17)C10B—C10A—H10A106.1
C2—C3—C3A104.03 (17)C5A—C10A—H10A106.1
C11—C3—H3A106.8C10A—C10B—C1120.45 (18)
C2—C3—H3A106.8C10A—C10B—C3A112.84 (16)
C3A—C3—H3A106.8C1—C10B—C3A105.65 (16)
C4—C3A—C14112.35 (16)C10A—C10B—H10B105.6
C4—C3A—C10B106.94 (16)C1—C10B—H10B105.6
C14—C3A—C10B112.05 (16)C3A—C10B—H10B105.6
C4—C3A—C3116.49 (17)C12—C11—C13109.3 (2)
C14—C3A—C3108.49 (16)C12—C11—C3110.2 (2)
C10B—C3A—C399.89 (15)C13—C11—C3114.5 (2)
C3A—C4—C5111.34 (17)C12—C11—H11107.5
C3A—C4—H4A109.4C13—C11—H11107.5
C5—C4—H4A109.4C3—C11—H11107.5
C3A—C4—H4B109.4C11—C12—H12A109.5
C5—C4—H4B109.4C11—C12—H12B109.5
H4A—C4—H4B108H12A—C12—H12B109.5
C4—C5—C5A115.89 (18)C11—C12—H12C109.5
C4—C5—H5A108.3H12A—C12—H12C109.5
C5A—C5—H5A108.3H12B—C12—H12C109.5
C4—C5—H5B108.3C11—C13—H13A109.5
C5A—C5—H5B108.3C11—C13—H13B109.5
H5A—C5—H5B107.4H13A—C13—H13B109.5
C15—C5A—C5108.27 (19)C11—C13—H13C109.5
C15—C5A—C6109.69 (18)H13A—C13—H13C109.5
C5—C5A—C6107.63 (18)H13B—C13—H13C109.5
C15—C5A—C10A109.16 (19)O2—C14—O1121.61 (18)
C5—C5A—C10A107.99 (17)O2—C14—C3A124.46 (18)
C6—C5A—C10A113.94 (17)O1—C14—C3A113.90 (17)
C7—C6—C5A120.54 (18)C5A—C15—H15A109.5
C7—C6—H6A107.2C5A—C15—H15B109.5
C5A—C6—H6A107.2H15A—C15—H15B109.5
C7—C6—H6B107.2C5A—C15—H15C109.5
C5A—C6—H6B107.2H15A—C15—H15C109.5
H6A—C6—H6B106.8H15B—C15—H15C109.5
O3—C7—C6108.13 (17)C8—C16—H16A109.5
O3—C7—C8110.08 (17)C8—C16—H16B109.5
C6—C7—C8116.42 (17)H16A—C16—H16B109.5
O3—C7—H7107.3C8—C16—H16C109.5
C6—C7—H7107.3H16A—C16—H16C109.5
C8—C7—H7107.3H16B—C16—H16C109.5
C10B—C1—C2—C38.2 (2)C9—C10—C10A—C10B−79.8 (3)
C1—C2—C3—C11149.26 (18)C9—C10—C10A—C5A47.8 (3)
C1—C2—C3—C3A18.8 (2)C15—C5A—C10A—C1060.6 (2)
C11—C3—C3A—C481.3 (2)C5—C5A—C10A—C10178.06 (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—C1479.8 (2)C5—C5A—C10A—C10B−53.2 (2)
C11—C3—C3A—C10B−164.02 (18)C6—C5A—C10A—C10B66.3 (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—C555.2 (2)C10—C10A—C10B—C3A−169.03 (16)
C3—C3A—C4—C5165.83 (16)C5A—C10A—C10B—C3A61.1 (2)
C3A—C4—C5—C5A−55.1 (2)C2—C1—C10B—C10A−162.12 (17)
C4—C5—C5A—C15170.12 (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—C10A52.0 (2)C14—C3A—C10B—C10A63.1 (2)
C15—C5A—C6—C7−56.7 (3)C3—C3A—C10B—C10A177.76 (15)
C5—C5A—C6—C7−174.27 (18)C4—C3A—C10B—C1165.97 (16)
C10A—C5A—C6—C766.0 (2)C14—C3A—C10B—C1−70.5 (2)
C5A—C6—C7—O3166.72 (16)C3—C3A—C10B—C144.2 (2)
C5A—C6—C7—C8−68.8 (2)C2—C3—C11—C1262.0 (3)
O3—C7—C8—O469.69 (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—C965.8 (2)C4—C3A—C14—O2165.1 (2)
O3—C7—C8—C16−48.1 (2)C10B—C3A—C14—O244.7 (3)
C6—C7—C8—C16−171.59 (18)C3—C3A—C14—O2−64.7 (3)
O4—C8—C9—C1067.3 (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—O1113.2 (2)
C8—C9—C10—C10A2.5 (4)
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.802.613 (3)170
O3—H3···O2ii0.822.012.825 (3)173
O4—H4···O3iii0.821.942.752 (3)172
C1—H1B···O20.972.442.889 (4)108
C5—H5B···O10.972.513.054 (4)116
C6—H6B···O40.972.522.901 (3)104
C16—H16A···O30.962.462.809 (4)101
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯O4i0.821.802.613 (3)170
O3—H3⋯O2ii0.822.012.825 (3)173
O4—H4⋯O3iii0.821.942.752 (3)172
C1—H1B⋯O20.972.442.889 (4)108
C5—H5B⋯O10.972.513.054 (4)116
C6—H6B⋯O40.972.522.901 (3)104
C16—H16A⋯O30.962.462.809 (4)101

Symmetry codes: (i) ; (ii) ; (iii) .

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Journal:  Phytother Res       Date:  2005-08       Impact factor: 5.878

3.  Mulinane-type diterpenoids from Azorella compacta display antiplasmodial activity.

Authors:  Luis A Loyola; Jorge Bórquez; Glauco Morales; Aurelio San-Martín; Jose Darias; Ninoska Flores; Alberto Giménez
Journal:  Phytochemistry       Date:  2004-07       Impact factor: 4.072

4.  Diterpenoids from Azorella compacta (Umbelliferae) active on Trypanosoma cruzi.

Authors:  Jorge E Araya; Iván Neira; Solange da Silva; Renato A Mortara; Patricio Manque; Esteban Cordero; Hernán Sagua; Alberto Loyola; Jorge Bórquez; Glauco Morales; Jorge González
Journal:  Mem Inst Oswaldo Cruz       Date:  2003-07-18       Impact factor: 2.743
  4 in total
  1 in total

1.  An orthorhombic polymorph of mulinic acid.

Authors:  Iván Brito; Jorge Bórquez; Luis Alberto Loyola; Matías López-Rodríguez; Alejandro Cárdenas
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-01-09
  1 in total

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