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The title compound, 4,4,8,11b-tetra­methyl-2,3,4,4a,5,6,6a,7,10a,11,11a,11b-dodeca­hydro-1H,9H-6a:7,10a:11-diepoxy­phen­anthro[3,2-b]furan-9-one, C20H26O4, a natural ent-abietane diterpenoid, is composed of four fused rings with the expected cis and trans junctions. In the crystal structure, the mol­ecules stack along the b axis and are linked by C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025171/su6216sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025171/su6216Isup2.hkl
Contains datablock I

CCDC reference: 283992

Key indicators

  • Single-crystal X-ray study
  • T = 286 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.088
  • Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.00 From the CIF: _reflns_number_total 2219 Count of symmetry unique reflns 2219 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.

4,4,8,11b-tetramethyl-2,3,4,4a,5,6,6a,7,10a,11,11a,11b-dodecahydro- 1H,9H-6a:7,10a:11-diepoxyphenanthro[3,2-b]furan-9-one top
Crystal data top
C20H26O4F(000) = 356
Mr = 330.41Dx = 1.255 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 27 reflections
a = 6.912 (1) Åθ = 3.1–14.4°
b = 10.751 (1) ŵ = 0.09 mm1
c = 12.080 (2) ÅT = 286 K
β = 103.18 (1)°Plate, colourless
V = 874.1 (2) Å30.54 × 0.46 × 0.24 mm
Z = 2
Data collection top
Siemens P4
diffractometer
Rint = 0.014
Radiation source: normal-focus sealed tubeθmax = 28.0°, θmin = 1.7°
Graphite monochromatorh = 09
ω scansk = 014
2505 measured reflectionsl = 1515
2219 independent reflections3 standard reflections every 97 reflections
1496 reflections with I > 2σ(I) intensity decay: 2.8%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0466P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
2219 reflectionsΔρmax = 0.16 e Å3
222 parametersΔρmin = 0.12 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.068 (5)
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.

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
xyzUiso*/Ueq
O10.4365 (3)0.38081 (18)0.59246 (15)0.0542 (5)
O20.7625 (3)0.23672 (16)0.55883 (15)0.0534 (5)
O30.5463 (3)0.57178 (18)0.68469 (14)0.0513 (5)
O40.7301 (4)0.6808 (2)0.83022 (17)0.0706 (6)
C10.4081 (3)0.5349 (3)0.2570 (2)0.0469 (7)
H1A0.32070.46430.23430.056*
H1B0.35070.58610.30730.056*
C20.4183 (4)0.6104 (3)0.1516 (2)0.0596 (8)
H2A0.28580.63750.11380.072*
H2B0.49950.68380.17390.072*
C30.5058 (4)0.5333 (3)0.0705 (2)0.0580 (8)
H3A0.51070.58320.00430.070*
H3B0.41940.46290.04500.070*
C40.7155 (4)0.4853 (3)0.1238 (2)0.0485 (7)
C50.7121 (3)0.4184 (2)0.23738 (19)0.0385 (6)
H50.62950.34450.21470.046*
C60.9149 (4)0.3670 (3)0.2992 (2)0.0467 (7)
H6A0.97830.32690.24480.056*
H6B0.99940.43490.33430.056*
C70.8911 (4)0.2744 (3)0.3893 (2)0.0513 (7)
H7A0.82490.20080.35250.062*
H7B1.02170.24960.43220.062*
C80.7742 (4)0.3248 (2)0.4701 (2)0.0412 (6)
C90.5803 (4)0.3922 (2)0.4147 (2)0.0371 (6)
H90.48800.32880.37520.044*
C100.6122 (3)0.4874 (2)0.32245 (18)0.0334 (5)
C110.4789 (4)0.4558 (2)0.4986 (2)0.0419 (6)
H110.38060.51970.46700.050*
C120.5846 (4)0.4728 (3)0.6167 (2)0.0423 (6)
C130.7947 (4)0.4389 (2)0.65686 (19)0.0413 (6)
C140.8792 (4)0.3487 (2)0.5901 (2)0.0445 (6)
H141.02410.33940.60890.053*
C150.8768 (4)0.5104 (3)0.74486 (19)0.0462 (7)
C160.7215 (4)0.5970 (3)0.7636 (2)0.0509 (7)
C171.0823 (4)0.5144 (3)0.8169 (2)0.0657 (9)
H17A1.08380.47800.88960.079*
H17B1.12610.59920.82700.079*
H17C1.16950.46850.78050.079*
C180.7678 (6)0.3883 (4)0.0415 (2)0.0838 (12)
H18A0.74230.42260.03390.101*
H18B0.68800.31530.04160.101*
H18C0.90580.36670.06540.101*
C190.8633 (4)0.5916 (3)0.1337 (2)0.0660 (9)
H19A0.99100.56440.17630.079*
H19B0.81870.66040.17200.079*
H19C0.87370.61710.05910.079*
C200.7349 (4)0.5964 (2)0.3841 (2)0.0449 (6)
H20A0.86170.56640.42530.054*
H20B0.66570.63360.43610.054*
H20C0.75400.65720.32940.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0521 (11)0.0604 (13)0.0538 (11)0.0093 (10)0.0201 (9)0.0073 (10)
O20.0731 (13)0.0363 (10)0.0520 (10)0.0046 (10)0.0170 (10)0.0119 (9)
O30.0559 (11)0.0561 (12)0.0438 (10)0.0110 (10)0.0151 (9)0.0008 (9)
O40.0987 (16)0.0635 (13)0.0486 (11)0.0055 (13)0.0148 (11)0.0095 (11)
C10.0322 (13)0.0585 (17)0.0493 (15)0.0053 (12)0.0078 (11)0.0102 (13)
C20.0370 (14)0.079 (2)0.0605 (17)0.0075 (16)0.0068 (13)0.0243 (17)
C30.0468 (15)0.083 (2)0.0416 (15)0.0040 (15)0.0047 (12)0.0162 (16)
C40.0444 (15)0.0630 (19)0.0386 (13)0.0047 (14)0.0106 (11)0.0075 (13)
C50.0350 (12)0.0402 (15)0.0402 (12)0.0017 (11)0.0082 (10)0.0019 (11)
C60.0428 (15)0.0531 (18)0.0458 (14)0.0110 (13)0.0134 (11)0.0033 (14)
C70.0603 (17)0.0451 (16)0.0488 (15)0.0174 (15)0.0130 (14)0.0029 (13)
C80.0504 (15)0.0321 (13)0.0425 (13)0.0062 (12)0.0137 (12)0.0067 (11)
C90.0357 (13)0.0340 (13)0.0399 (12)0.0040 (11)0.0052 (10)0.0003 (11)
C100.0281 (11)0.0335 (13)0.0370 (12)0.0015 (10)0.0038 (9)0.0027 (10)
C110.0366 (13)0.0460 (15)0.0436 (12)0.0032 (12)0.0105 (10)0.0074 (13)
C120.0431 (14)0.0459 (16)0.0401 (13)0.0004 (13)0.0142 (11)0.0034 (12)
C130.0476 (14)0.0412 (15)0.0348 (12)0.0029 (13)0.0085 (11)0.0120 (12)
C140.0471 (15)0.0422 (15)0.0430 (14)0.0069 (13)0.0078 (11)0.0083 (13)
C150.0558 (16)0.0482 (16)0.0340 (13)0.0018 (14)0.0088 (12)0.0093 (12)
C160.0690 (18)0.0494 (16)0.0351 (13)0.0029 (16)0.0136 (13)0.0078 (14)
C170.0622 (18)0.081 (2)0.0470 (15)0.0021 (18)0.0026 (14)0.0083 (17)
C180.109 (3)0.103 (3)0.0466 (16)0.020 (3)0.0314 (18)0.007 (2)
C190.0404 (15)0.092 (2)0.0663 (18)0.0041 (17)0.0142 (13)0.0320 (19)
C200.0476 (14)0.0370 (14)0.0491 (14)0.0070 (13)0.0091 (11)0.0044 (13)
Geometric parameters (Å, º) top
O1—C121.405 (3)C7—H7B0.9700
O1—C111.475 (3)C8—C141.487 (3)
O2—C81.446 (3)C8—C91.537 (3)
O2—C141.450 (3)C9—C111.520 (4)
O3—C161.386 (3)C9—C101.566 (3)
O3—C121.406 (3)C9—H90.9800
O4—C161.200 (3)C10—C201.535 (3)
C1—C21.526 (3)C11—C121.459 (3)
C1—C101.539 (3)C11—H110.9800
C1—H1A0.9700C12—C131.469 (3)
C1—H1B0.9700C13—C151.330 (3)
C2—C31.511 (4)C13—C141.466 (3)
C2—H2A0.9700C14—H140.9800
C2—H2B0.9700C15—C161.477 (4)
C3—C41.535 (4)C15—C171.487 (4)
C3—H3A0.9700C17—H17A0.9600
C3—H3B0.9700C17—H17B0.9600
C4—C191.519 (4)C17—H17C0.9600
C4—C181.539 (4)C18—H18A0.9600
C4—C51.554 (3)C18—H18B0.9600
C5—C61.533 (3)C18—H18C0.9600
C5—C101.552 (3)C19—H19A0.9600
C5—H50.9800C19—H19B0.9600
C6—C71.512 (3)C19—H19C0.9600
C6—H6A0.9700C20—H20A0.9600
C6—H6B0.9700C20—H20B0.9600
C7—C81.503 (3)C20—H20C0.9600
C7—H7A0.9700
C12—O1—C1160.81 (15)C20—C10—C1109.7 (2)
C8—O2—C1461.81 (15)C20—C10—C5113.99 (19)
C16—O3—C12107.4 (2)C1—C10—C5108.22 (18)
C2—C1—C10113.2 (2)C20—C10—C9107.79 (18)
C2—C1—H1A108.9C1—C10—C9108.71 (18)
C10—C1—H1A108.9C5—C10—C9108.34 (19)
C2—C1—H1B108.9C12—C11—O157.24 (15)
C10—C1—H1B108.9C12—C11—C9120.3 (2)
H1A—C1—H1B107.8O1—C11—C9118.0 (2)
C3—C2—C1110.5 (3)C12—C11—H11116.2
C3—C2—H2A109.5O1—C11—H11116.2
C1—C2—H2A109.5C9—C11—H11116.2
C3—C2—H2B109.5O1—C12—O3115.43 (19)
C1—C2—H2B109.5O1—C12—C1161.94 (16)
H2A—C2—H2B108.1O3—C12—C11123.2 (2)
C2—C3—C4113.1 (2)O1—C12—C13120.8 (2)
C2—C3—H3A109.0O3—C12—C13107.4 (2)
C4—C3—H3A109.0C11—C12—C13121.9 (2)
C2—C3—H3B109.0C15—C13—C14132.2 (3)
C4—C3—H3B109.0C15—C13—C12109.3 (2)
H3A—C3—H3B107.8C14—C13—C12118.1 (2)
C19—C4—C3109.5 (2)O2—C14—C13115.1 (2)
C19—C4—C18107.9 (2)O2—C14—C858.95 (15)
C3—C4—C18107.2 (2)C13—C14—C8118.9 (2)
C19—C4—C5115.0 (2)O2—C14—H14117.0
C3—C4—C5108.9 (2)C13—C14—H14117.0
C18—C4—C5108.0 (2)C8—C14—H14117.0
C6—C5—C10110.20 (18)C13—C15—C16107.1 (2)
C6—C5—C4113.6 (2)C13—C15—C17131.3 (3)
C10—C5—C4117.5 (2)C16—C15—C17121.5 (3)
C6—C5—H5104.7O4—C16—O3120.6 (3)
C10—C5—H5104.7O4—C16—C15130.5 (3)
C4—C5—H5104.7O3—C16—C15108.8 (2)
C7—C6—C5110.5 (2)C15—C17—H17A109.5
C7—C6—H6A109.5C15—C17—H17B109.5
C5—C6—H6A109.5H17A—C17—H17B109.5
C7—C6—H6B109.5C15—C17—H17C109.5
C5—C6—H6B109.5H17A—C17—H17C109.5
H6A—C6—H6B108.1H17B—C17—H17C109.5
C8—C7—C6113.1 (2)C4—C18—H18A109.5
C8—C7—H7A108.9C4—C18—H18B109.5
C6—C7—H7A108.9H18A—C18—H18B109.5
C8—C7—H7B108.9C4—C18—H18C109.5
C6—C7—H7B108.9H18A—C18—H18C109.5
H7A—C7—H7B107.8H18B—C18—H18C109.5
O2—C8—C1459.24 (15)C4—C19—H19A109.5
O2—C8—C7112.0 (2)C4—C19—H19B109.5
C14—C8—C7118.7 (2)H19A—C19—H19B109.5
O2—C8—C9116.2 (2)C4—C19—H19C109.5
C14—C8—C9121.8 (2)H19A—C19—H19C109.5
C7—C8—C9115.6 (2)H19B—C19—H19C109.5
C11—C9—C8114.28 (19)C10—C20—H20A109.5
C11—C9—C10109.96 (19)C10—C20—H20B109.5
C8—C9—C10111.59 (19)H20A—C20—H20B109.5
C11—C9—H9106.9C10—C20—H20C109.5
C8—C9—H9106.9H20A—C20—H20C109.5
C10—C9—H9106.9H20B—C20—H20C109.5
C10—C1—C2—C359.0 (3)C8—C9—C11—C1213.0 (3)
C1—C2—C3—C458.7 (3)C10—C9—C11—C12113.4 (2)
C2—C3—C4—C1974.4 (3)C8—C9—C11—O153.4 (3)
C2—C3—C4—C18168.8 (3)C10—C9—C11—O1179.83 (18)
C2—C3—C4—C552.2 (3)C11—O1—C12—O3115.7 (2)
C19—C4—C5—C656.3 (3)C11—O1—C12—C13112.3 (3)
C3—C4—C5—C6179.6 (2)C16—O3—C12—O1137.3 (2)
C18—C4—C5—C664.4 (3)C16—O3—C12—C11150.9 (2)
C19—C4—C5—C1074.5 (3)C16—O3—C12—C130.7 (2)
C3—C4—C5—C1048.8 (3)C9—C11—C12—O1105.7 (2)
C18—C4—C5—C10164.9 (2)O1—C11—C12—O3103.5 (2)
C10—C5—C6—C761.4 (3)C9—C11—C12—O3150.8 (2)
C4—C5—C6—C7164.3 (2)O1—C11—C12—C13110.6 (3)
C5—C6—C7—C853.0 (3)C9—C11—C12—C134.9 (4)
C14—O2—C8—C7111.2 (2)O1—C12—C13—C15133.9 (2)
C14—O2—C8—C9113.0 (2)O3—C12—C13—C151.4 (3)
C6—C7—C8—O2177.0 (2)C11—C12—C13—C15151.9 (2)
C6—C7—C8—C14111.1 (3)O1—C12—C13—C1452.7 (3)
C6—C7—C8—C946.9 (3)O3—C12—C13—C14171.98 (19)
O2—C8—C9—C1153.0 (3)C11—C12—C13—C1421.4 (4)
C14—C8—C9—C1115.6 (3)C8—O2—C14—C13109.9 (2)
C7—C8—C9—C11172.8 (2)C15—C13—C14—O2140.0 (3)
O2—C8—C9—C10178.49 (19)C12—C13—C14—O248.5 (3)
C14—C8—C9—C10110.0 (2)C15—C13—C14—C8153.1 (3)
C7—C8—C9—C1047.2 (3)C12—C13—C14—C818.4 (3)
C2—C1—C10—C2072.6 (3)C7—C8—C14—O299.9 (2)
C2—C1—C10—C552.3 (3)C9—C8—C14—O2103.6 (2)
C2—C1—C10—C9169.8 (2)O2—C8—C14—C13103.5 (2)
C6—C5—C10—C2058.8 (3)C7—C8—C14—C13156.6 (2)
C4—C5—C10—C2073.5 (3)C9—C8—C14—C130.1 (3)
C6—C5—C10—C1178.9 (2)C14—C13—C15—C16170.7 (2)
C4—C5—C10—C148.8 (3)C12—C13—C15—C161.4 (3)
C6—C5—C10—C961.2 (2)C14—C13—C15—C178.4 (5)
C4—C5—C10—C9166.51 (19)C12—C13—C15—C17179.5 (3)
C11—C9—C10—C2057.3 (2)C12—O3—C16—O4177.8 (2)
C8—C9—C10—C2070.6 (2)C12—O3—C16—C150.1 (2)
C11—C9—C10—C161.5 (2)C13—C15—C16—O4176.7 (3)
C8—C9—C10—C1170.6 (2)C17—C15—C16—O42.5 (4)
C11—C9—C10—C5178.91 (18)C13—C15—C16—O30.9 (3)
C8—C9—C10—C553.2 (2)C17—C15—C16—O3179.9 (2)
C12—O1—C11—C9109.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O2i0.972.543.499 (3)173
C11—H11···O2i0.982.533.444 (3)156
Symmetry code: (i) x+1, y+1/2, z+1.
 

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