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The X-ray structure of di­methyl (Z)-[(8aS,2R,4aR,4bR)-8a-methoxy­carbonyl-1,4a,7-tri­methyl-8-oxo-2,3,4,4a,4b,5,8,8a,9,10-deca­hydro­phenanthren-2-yl]-2-butenedioate, C25H32O7, confirmed its relative configuration. The structure shows the bend in the molecular skeleton as found for similar compounds. Weak intermolecular C—H...O interactions have been found in the crystal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008510/ob6041sup1.cif
Contains datablocks I, abad01

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008510/ob6041Isup2.hkl
Contains datablock I

CCDC reference: 170315

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.049
  • wR factor = 0.123
  • Data-to-parameter ratio = 14.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack 0.500 From the CIF: _refine_ls_abs_structure_Flack_su 1.600 Alert C Flack test results are ambiguous. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.98 From the CIF: _reflns_number_total 4163 Count of symmetry unique reflns 2372 Completeness (_total/calc) 175.51% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1791 Fraction of Friedel pairs measured 0.755 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: MolEN (Fair, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.

dimethyl(Z)-[(8aS,2R, 4aR, 4bR)-8a-methoxycarbonyl-1,4a,7- -trimethyl-8-oxo-2,3,4,4a,4 b,5,8,8a,9,10-decahydro- -phenanthren-2-yl]-2-butenedioate top
Crystal data top
C25H32O7Dx = 1.238 Mg m3
Mr = 444.51Melting point: 430 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 11.810 (2) ÅCell parameters from 25 reflections
b = 13.985 (3) Åθ = 10–12°
c = 14.434 (3) ŵ = 0.09 mm1
V = 2384.0 (8) Å3T = 293 K
Z = 4Block, colourless
F(000) = 9520.64 × 0.62 × 0.44 mm
Data collection top
Nonius-CAD4
diffractometer
Rint = 0.030
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.2°
Graphite monochromatorh = 144
ω–scansk = 1616
6144 measured reflectionsl = 017
4163 independent reflections3 standard reflections every 250 reflections
3049 reflections with I > 2σ(I) intensity decay: 1.8%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0417P)2 + 0.6085P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.15 e Å3
4163 reflectionsΔρmin = 0.14 e Å3
290 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0069 (9)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.5 (16)
Special details top

Experimental. crystal source: slow evaporation of a methanol solution

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. Absolute structure could not be determined.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1392 (3)0.0672 (2)1.05093 (19)0.0489 (8)
H1A0.21090.03381.04610.059*
H1B0.15320.13451.03970.059*
C20.0924 (3)0.0547 (3)1.1484 (2)0.0566 (9)
H2A0.14810.07591.19340.068*
H2B0.07650.01231.15980.068*
C30.0159 (3)0.1131 (2)1.1591 (2)0.0538 (8)
H30.05280.09141.21620.065*
C40.0973 (3)0.0943 (2)1.0808 (2)0.0508 (8)
C50.0649 (3)0.0539 (2)1.0013 (2)0.0461 (8)
C60.1476 (3)0.0318 (2)0.9250 (2)0.0504 (8)
H6A0.22290.05110.94420.061*
H6B0.14890.03670.91440.061*
C70.1176 (2)0.0824 (2)0.8348 (2)0.0470 (8)
H7A0.12520.15080.84350.056*
H7B0.17060.06310.78710.056*
C80.0028 (2)0.0601 (2)0.80256 (18)0.0414 (7)
C90.0862 (2)0.0800 (2)0.88366 (19)0.0407 (7)
H90.07550.14800.89730.049*
C100.0581 (3)0.0290 (2)0.97680 (19)0.0436 (7)
C110.2096 (3)0.0729 (2)0.8537 (2)0.0497 (8)
H11A0.25750.09790.90260.060*
H11B0.22910.00630.84440.060*
C120.2316 (3)0.1270 (2)0.7665 (2)0.0506 (8)
H120.30640.14240.75300.061*
C130.1529 (3)0.1547 (2)0.7068 (2)0.0479 (8)
C140.0340 (3)0.1256 (2)0.7200 (2)0.0467 (8)
C150.0095 (3)0.2193 (2)1.17131 (19)0.0496 (8)
C160.0009 (3)0.2845 (2)1.1048 (2)0.0546 (8)
H160.01890.26391.04570.066*
C170.0209 (3)0.3866 (3)1.1190 (2)0.0582 (9)
C180.0267 (5)0.5370 (3)1.0456 (3)0.1009 (16)
H18A0.04020.56431.07250.121*
H18B0.03790.56310.98470.121*
H18C0.09100.55171.08370.121*
C190.0418 (3)0.2478 (2)1.2682 (2)0.0514 (8)
C200.1881 (4)0.2968 (4)1.3663 (3)0.0950 (15)
H20A0.15650.35901.37710.114*
H20B0.26930.30071.36780.114*
H20C0.16260.25351.41350.114*
C210.2177 (3)0.1226 (3)1.1025 (3)0.0776 (12)
H21A0.25190.15031.04840.093*
H21B0.21800.16861.15190.093*
H21C0.25990.06711.12100.093*
C220.0040 (3)0.0412 (2)0.7622 (2)0.0486 (7)
C230.1085 (3)0.1566 (2)0.6815 (3)0.0732 (11)
H23A0.10190.20540.72790.088*
H23B0.17940.16340.64970.088*
H23C0.04740.16260.63800.088*
C240.0727 (3)0.0805 (2)0.9710 (2)0.0562 (9)
H24A0.05980.10821.03090.067*
H24B0.14810.09530.95080.067*
H24C0.01910.10620.92760.067*
C250.1791 (3)0.2122 (3)0.6216 (2)0.0693 (11)
H25A0.14400.27390.62640.083*
H25B0.15050.17950.56800.083*
H25C0.25960.21980.61600.083*
O10.0376 (3)0.42510 (18)1.19113 (17)0.0860 (9)
O20.0137 (3)0.43439 (18)1.03911 (15)0.0787 (8)
O30.0243 (2)0.2513 (2)1.33007 (16)0.0729 (7)
O40.1522 (2)0.26248 (19)1.27701 (16)0.0682 (7)
O50.0754 (2)0.09320 (18)0.75892 (19)0.0779 (8)
O60.10348 (19)0.06377 (15)0.72505 (17)0.0628 (6)
O70.0391 (2)0.14819 (18)0.66556 (15)0.0675 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0502 (18)0.0511 (18)0.0454 (18)0.0033 (16)0.0013 (14)0.0009 (15)
C20.071 (2)0.0552 (19)0.0433 (17)0.0044 (18)0.0040 (17)0.0019 (15)
C30.067 (2)0.0583 (19)0.0364 (15)0.0005 (17)0.0094 (17)0.0065 (14)
C40.0510 (19)0.0519 (19)0.0495 (18)0.0072 (16)0.0025 (16)0.0015 (15)
C50.0472 (18)0.0436 (17)0.0475 (17)0.0021 (15)0.0043 (15)0.0084 (14)
C60.0387 (18)0.0568 (19)0.0558 (19)0.0030 (15)0.0027 (16)0.0031 (16)
C70.0419 (17)0.0483 (18)0.0509 (18)0.0001 (15)0.0029 (15)0.0019 (15)
C80.0417 (16)0.0386 (15)0.0438 (15)0.0016 (14)0.0025 (14)0.0013 (12)
C90.0387 (16)0.0401 (16)0.0435 (15)0.0023 (13)0.0019 (14)0.0027 (13)
C100.0452 (18)0.0447 (16)0.0410 (16)0.0015 (15)0.0000 (14)0.0027 (14)
C110.0420 (18)0.059 (2)0.0480 (17)0.0023 (16)0.0025 (14)0.0041 (16)
C120.0464 (18)0.0515 (18)0.0540 (18)0.0031 (15)0.0085 (16)0.0083 (16)
C130.056 (2)0.0437 (17)0.0445 (17)0.0006 (15)0.0048 (16)0.0004 (15)
C140.054 (2)0.0469 (17)0.0393 (16)0.0064 (15)0.0036 (16)0.0023 (14)
C150.055 (2)0.0556 (18)0.0378 (15)0.0013 (17)0.0058 (16)0.0025 (14)
C160.068 (2)0.0574 (19)0.0384 (15)0.0030 (19)0.0033 (17)0.0025 (15)
C170.067 (2)0.062 (2)0.0457 (18)0.0076 (18)0.0080 (18)0.0052 (16)
C180.145 (5)0.057 (3)0.101 (3)0.012 (3)0.005 (3)0.021 (2)
C190.057 (2)0.0560 (19)0.0414 (17)0.0039 (16)0.0028 (17)0.0006 (15)
C200.079 (3)0.146 (4)0.060 (2)0.021 (3)0.012 (2)0.009 (3)
C210.058 (2)0.100 (3)0.075 (3)0.001 (2)0.017 (2)0.023 (2)
C220.0527 (19)0.0460 (17)0.0471 (17)0.0038 (16)0.0068 (17)0.0006 (14)
C230.080 (3)0.047 (2)0.093 (3)0.0064 (19)0.014 (2)0.019 (2)
C240.068 (2)0.0452 (18)0.0551 (18)0.0052 (17)0.0004 (18)0.0044 (15)
C250.081 (3)0.068 (2)0.059 (2)0.001 (2)0.015 (2)0.0085 (19)
O10.143 (3)0.0613 (15)0.0538 (14)0.0039 (17)0.0062 (16)0.0079 (13)
O20.118 (2)0.0643 (16)0.0541 (13)0.0058 (16)0.0000 (16)0.0117 (12)
O30.0622 (16)0.114 (2)0.0423 (12)0.0046 (15)0.0130 (13)0.0125 (13)
O40.0548 (15)0.102 (2)0.0480 (13)0.0047 (14)0.0018 (12)0.0085 (13)
O50.0629 (16)0.0735 (17)0.097 (2)0.0190 (14)0.0018 (15)0.0292 (15)
O60.0605 (15)0.0421 (12)0.0857 (17)0.0020 (11)0.0148 (13)0.0144 (12)
O70.0631 (16)0.0897 (18)0.0498 (13)0.0130 (14)0.0058 (12)0.0155 (13)
Geometric parameters (Å, º) top
C1—C21.522 (4)C13—C251.501 (4)
C1—C101.532 (4)C14—O71.209 (4)
C1—H1A0.9700C15—C161.328 (4)
C1—H1B0.9700C15—C191.504 (4)
C2—C31.525 (5)C16—C171.463 (5)
C2—H2A0.9700C16—H160.9300
C2—H2B0.9700C17—O11.188 (4)
C3—C41.508 (5)C17—O21.335 (4)
C3—C151.525 (4)C18—O21.446 (5)
C3—H30.9800C18—H18A0.9600
C4—C51.335 (4)C18—H18B0.9600
C4—C211.509 (5)C18—H18C0.9600
C5—C61.505 (4)C19—O31.187 (4)
C5—C101.535 (4)C19—O41.326 (4)
C6—C71.523 (4)C20—O41.439 (4)
C6—H6A0.9700C20—H20A0.9600
C6—H6B0.9700C20—H20B0.9600
C7—C81.528 (4)C20—H20C0.9600
C7—H7A0.9700C21—H21A0.9600
C7—H7B0.9700C21—H21B0.9600
C8—C221.532 (4)C21—H21C0.9600
C8—C141.547 (4)C22—O51.188 (4)
C8—C91.555 (4)C22—O61.329 (4)
C9—C111.522 (4)C23—O61.443 (4)
C9—C101.558 (4)C23—H23A0.9600
C9—H90.9800C23—H23B0.9600
C10—C241.543 (4)C23—H23C0.9600
C11—C121.491 (4)C24—H24A0.9600
C11—H11A0.9700C24—H24B0.9600
C11—H11B0.9700C24—H24C0.9600
C12—C131.325 (4)C25—H25A0.9600
C12—H120.9300C25—H25B0.9600
C13—C141.475 (4)C25—H25C0.9600
C2—C1—C10112.3 (3)C11—C12—H12117.5
C2—C1—H1A109.1C12—C13—C14120.2 (3)
C10—C1—H1A109.1C12—C13—C25123.0 (3)
C2—C1—H1B109.1C14—C13—C25116.8 (3)
C10—C1—H1B109.1O7—C14—C13121.5 (3)
H1A—C1—H1B107.9O7—C14—C8119.0 (3)
C1—C2—C3109.7 (3)C13—C14—C8119.3 (3)
C1—C2—H2A109.7C16—C15—C19120.7 (3)
C3—C2—H2A109.7C16—C15—C3124.7 (3)
C1—C2—H2B109.7C19—C15—C3114.5 (3)
C3—C2—H2B109.7C15—C16—C17123.8 (3)
H2A—C2—H2B108.2C15—C16—H16118.1
C4—C3—C2111.4 (3)C17—C16—H16118.1
C4—C3—C15112.5 (3)O1—C17—O2122.8 (3)
C2—C3—C15111.6 (3)O1—C17—C16126.3 (3)
C4—C3—H3107.0O2—C17—C16110.9 (3)
C2—C3—H3107.0O2—C18—H18A109.5
C15—C3—H3107.0O2—C18—H18B109.5
C5—C4—C3122.3 (3)H18A—C18—H18B109.5
C5—C4—C21124.1 (3)O2—C18—H18C109.5
C3—C4—C21113.6 (3)H18A—C18—H18C109.5
C4—C5—C6122.0 (3)H18B—C18—H18C109.5
C4—C5—C10124.5 (3)O3—C19—O4124.7 (3)
C6—C5—C10113.5 (3)O3—C19—C15122.9 (3)
C5—C6—C7112.2 (3)O4—C19—C15112.3 (3)
C5—C6—H6A109.2O4—C20—H20A109.5
C7—C6—H6A109.2O4—C20—H20B109.5
C5—C6—H6B109.2H20A—C20—H20B109.5
C7—C6—H6B109.2O4—C20—H20C109.5
H6A—C6—H6B107.9H20A—C20—H20C109.5
C6—C7—C8112.5 (2)H20B—C20—H20C109.5
C6—C7—H7A109.1C4—C21—H21A109.5
C8—C7—H7A109.1C4—C21—H21B109.5
C6—C7—H7B109.1H21A—C21—H21B109.5
C8—C7—H7B109.1C4—C21—H21C109.5
H7A—C7—H7B107.8H21A—C21—H21C109.5
C7—C8—C22108.3 (2)H21B—C21—H21C109.5
C7—C8—C14109.6 (2)O5—C22—O6122.5 (3)
C22—C8—C14104.6 (2)O5—C22—C8125.0 (3)
C7—C8—C9108.9 (2)O6—C22—C8112.4 (3)
C22—C8—C9116.5 (2)O6—C23—H23A109.5
C14—C8—C9108.8 (2)O6—C23—H23B109.5
C11—C9—C8112.4 (2)H23A—C23—H23B109.5
C11—C9—C10114.8 (2)O6—C23—H23C109.5
C8—C9—C10115.6 (2)H23A—C23—H23C109.5
C11—C9—H9104.1H23B—C23—H23C109.5
C8—C9—H9104.1C10—C24—H24A109.5
C10—C9—H9104.1C10—C24—H24B109.5
C1—C10—C5110.5 (2)H24A—C24—H24B109.5
C1—C10—C24108.4 (3)C10—C24—H24C109.5
C5—C10—C24110.1 (3)H24A—C24—H24C109.5
C1—C10—C9108.1 (2)H24B—C24—H24C109.5
C5—C10—C9107.2 (2)C13—C25—H25A109.5
C24—C10—C9112.6 (2)C13—C25—H25B109.5
C12—C11—C9111.9 (3)H25A—C25—H25B109.5
C12—C11—H11A109.2C13—C25—H25C109.5
C9—C11—H11A109.2H25A—C25—H25C109.5
C12—C11—H11B109.2H25B—C25—H25C109.5
C9—C11—H11B109.2C17—O2—C18115.7 (3)
H11A—C11—H11B107.9C19—O4—C20115.3 (3)
C13—C12—C11125.1 (3)C22—O6—C23115.2 (3)
C13—C12—H12117.5
C10—C1—C2—C363.1 (4)C10—C9—C11—C12177.4 (2)
C1—C2—C3—C449.8 (4)C9—C11—C12—C1318.4 (4)
C1—C2—C3—C1576.8 (3)C11—C12—C13—C145.2 (5)
C2—C3—C4—C517.5 (4)C11—C12—C13—C25177.7 (3)
C15—C3—C4—C5108.6 (3)C12—C13—C14—O7178.4 (3)
C2—C3—C4—C21160.8 (3)C25—C13—C14—O71.2 (4)
C15—C3—C4—C2173.0 (4)C12—C13—C14—C81.7 (4)
C3—C4—C5—C6177.5 (3)C25—C13—C14—C8175.6 (3)
C21—C4—C5—C60.7 (5)C7—C8—C14—O734.1 (4)
C3—C4—C5—C104.7 (5)C22—C8—C14—O781.8 (3)
C21—C4—C5—C10177.1 (3)C9—C8—C14—O7153.1 (3)
C4—C5—C6—C7121.0 (3)C7—C8—C14—C13149.1 (3)
C10—C5—C6—C757.0 (4)C22—C8—C14—C1395.0 (3)
C5—C6—C7—C855.6 (4)C9—C8—C14—C1330.1 (3)
C6—C7—C8—C2275.3 (3)C4—C3—C15—C1624.9 (5)
C6—C7—C8—C14171.1 (2)C2—C3—C15—C16101.2 (4)
C6—C7—C8—C952.2 (3)C4—C3—C15—C19152.7 (3)
C7—C8—C9—C11172.1 (2)C2—C3—C15—C1981.2 (3)
C22—C8—C9—C1165.2 (3)C19—C15—C16—C170.2 (5)
C14—C8—C9—C1152.7 (3)C3—C15—C16—C17177.2 (3)
C7—C8—C9—C1053.5 (3)C15—C16—C17—O16.7 (6)
C22—C8—C9—C1069.2 (3)C15—C16—C17—O2175.9 (3)
C14—C8—C9—C10172.9 (2)C16—C15—C19—O3105.0 (4)
C2—C1—C10—C540.0 (4)C3—C15—C19—O372.6 (4)
C2—C1—C10—C2480.7 (3)C16—C15—C19—O478.7 (4)
C2—C1—C10—C9157.1 (3)C3—C15—C19—O4103.6 (3)
C4—C5—C10—C16.6 (4)C7—C8—C22—O51.4 (4)
C6—C5—C10—C1171.4 (2)C14—C8—C22—O5118.2 (3)
C4—C5—C10—C24113.1 (3)C9—C8—C22—O5121.6 (3)
C6—C5—C10—C2468.9 (3)C7—C8—C22—O6174.6 (2)
C4—C5—C10—C9124.1 (3)C14—C8—C22—O657.8 (3)
C6—C5—C10—C953.8 (3)C9—C8—C22—O662.4 (3)
C11—C9—C10—C154.1 (3)O1—C17—O2—C180.4 (6)
C8—C9—C10—C1172.6 (2)C16—C17—O2—C18177.2 (3)
C11—C9—C10—C5173.2 (3)O3—C19—O4—C208.2 (5)
C8—C9—C10—C553.4 (3)C15—C19—O4—C20175.6 (3)
C11—C9—C10—C2465.6 (3)O5—C22—O6—C230.8 (5)
C8—C9—C10—C2467.8 (3)C8—C22—O6—C23177.0 (3)
C8—C9—C11—C1247.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18B···O7i0.962.473.424 (5)170
C20—H20B···O7ii0.962.423.344 (5)161
C25—H25C···O3ii0.962.703.607 (5)158
C24—H24A···O3iii0.962.843.755 (4)160
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x+1/2, y+1/2, z+2; (iii) x, y1/2, z+5/2.
 

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