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In the molecular structure of the title compound, C20H24O6, there are eight chiral C atoms. Since an enantiomerically pure starting material was used, it can be confirmed that the synthesis of the title compound is stereoselective. There is an intermolecular hydrogen bond in the structure, leading to the formation of two-dimensional molecular layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014849/hg6055sup1.cif
Contains datablocks global, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014849/hg60553sup2.hkl
Contains datablock 3

CCDC reference: 245343

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.060
  • wR factor = 0.141
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A .. O6 .. 2.68 Ang.
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 25.99 From the CIF: _reflns_number_total 1989 Count of symmetry unique reflns 1989 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 2 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and Mercury (Version 1.2.1; Bruno et al., 2002).

(3aS,4S,5R,7aS,1'R,2a'S,6'S,6a'S)-5-(2',5'-dioxo-2a'-methyl-6', 6a'-epoxylperhydroinden-1'-yl)-3a,4-epoxy-5-hydroxy-7a-methyl- perhydro-1H-inden-1-one top
Crystal data top
C20H24O6Dx = 1.384 Mg m3
Mr = 360.39Melting point: 454.2-456.2 K K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 685 reflections
a = 6.8847 (12) Åθ = 2.6–19.3°
b = 9.4841 (17) ŵ = 0.10 mm1
c = 26.480 (5) ÅT = 293 K
V = 1729.0 (5) Å3Prism, white
Z = 40.32 × 0.23 × 0.20 mm
F(000) = 768
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1989 independent reflections
Radiation source: sealed tube1455 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.096
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 88
Tmin = 0.96, Tmax = 0.97k = 116
9425 measured reflectionsl = 3231
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
1989 reflections(Δ/σ)max < 0.001
239 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.55 e Å3
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
xyzUiso*/Ueq
C10.4547 (6)0.4983 (4)0.06840 (15)0.0366 (10)
C20.6051 (6)0.5380 (5)0.03234 (16)0.0459 (12)
H20.73890.50890.03950.055*
C30.5460 (7)0.5519 (5)0.02134 (16)0.0426 (11)
C40.3370 (7)0.5829 (6)0.03317 (17)0.0565 (14)
H4A0.29230.51370.05750.068*
H4B0.33070.67450.04940.068*
C50.1935 (7)0.5833 (6)0.01169 (16)0.0505 (13)
H5A0.19180.67620.02700.061*
H5B0.06370.56310.00060.061*
C60.2496 (5)0.4753 (5)0.05093 (14)0.0338 (10)
C70.1408 (6)0.4850 (5)0.10001 (15)0.0382 (11)
C80.2792 (5)0.4670 (5)0.14375 (14)0.0324 (10)
H80.29210.55930.16000.039*
C90.4759 (6)0.4331 (5)0.11928 (15)0.0413 (11)
H9A0.58230.47530.13800.050*
H9B0.49670.33220.11690.050*
C100.2135 (6)0.3624 (4)0.18485 (15)0.0314 (10)
C110.0357 (6)0.4139 (4)0.21360 (14)0.0342 (10)
H11A0.04830.46400.19030.041*
H11B0.03550.33250.22580.041*
C120.0793 (6)0.5101 (5)0.25819 (14)0.0362 (10)
H12A0.14600.59380.24630.043*
H12B0.04160.53940.27380.043*
C130.2042 (6)0.4357 (4)0.29694 (14)0.0314 (10)
C140.3823 (6)0.3749 (4)0.27282 (15)0.0326 (10)
C150.3879 (6)0.3392 (5)0.21972 (16)0.0366 (10)
H150.47870.26460.20990.044*
C160.5179 (6)0.3354 (5)0.31490 (16)0.0444 (12)
H16A0.65130.33000.30330.053*
H16B0.48150.24620.33010.053*
C170.4888 (6)0.4584 (5)0.35165 (15)0.0446 (11)
H17A0.48620.42470.38620.054*
H17B0.59330.52640.34830.054*
C180.2968 (6)0.5248 (5)0.33784 (14)0.0376 (10)
C190.2259 (8)0.3238 (6)0.0317 (2)0.0658 (16)
H19A0.09110.30510.02540.099*
H19B0.27380.25920.05670.099*
H19C0.29820.31230.00100.099*
C200.0892 (7)0.3213 (5)0.32566 (16)0.0435 (12)
H20A0.04860.24930.30250.065*
H20B0.02290.36300.34120.065*
H20C0.17040.28030.35120.065*
O10.5190 (5)0.6429 (3)0.06442 (11)0.0515 (9)
O20.6623 (5)0.5347 (4)0.05437 (12)0.0670 (11)
O30.0302 (4)0.5057 (4)0.10339 (11)0.0536 (9)
O40.1793 (4)0.2289 (3)0.16204 (11)0.0426 (8)
H40.06660.22480.15220.064*
O50.4722 (4)0.4685 (3)0.23673 (9)0.0345 (7)
O60.2301 (5)0.6311 (3)0.35592 (12)0.0512 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.033 (2)0.037 (3)0.039 (2)0.001 (2)0.0008 (19)0.002 (2)
C20.033 (2)0.057 (3)0.047 (3)0.003 (2)0.002 (2)0.005 (3)
C30.047 (3)0.039 (3)0.042 (2)0.004 (2)0.005 (2)0.002 (2)
C40.050 (3)0.076 (4)0.044 (3)0.000 (3)0.003 (2)0.007 (3)
C50.040 (3)0.070 (3)0.041 (3)0.009 (3)0.002 (2)0.008 (3)
C60.028 (2)0.039 (2)0.035 (2)0.000 (2)0.0017 (19)0.002 (2)
C70.030 (2)0.044 (3)0.042 (2)0.001 (2)0.001 (2)0.005 (2)
C80.030 (2)0.032 (2)0.035 (2)0.001 (2)0.0000 (18)0.003 (2)
C90.031 (2)0.049 (3)0.044 (2)0.000 (2)0.002 (2)0.010 (2)
C100.031 (2)0.029 (2)0.034 (2)0.0017 (19)0.0004 (19)0.0042 (19)
C110.035 (2)0.034 (2)0.035 (2)0.000 (2)0.0010 (19)0.0038 (19)
C120.033 (2)0.036 (2)0.039 (2)0.002 (2)0.0006 (19)0.003 (2)
C130.031 (2)0.030 (2)0.033 (2)0.0005 (19)0.0019 (18)0.0011 (19)
C140.034 (2)0.030 (2)0.034 (2)0.003 (2)0.0002 (18)0.007 (2)
C150.034 (2)0.032 (2)0.043 (2)0.003 (2)0.002 (2)0.003 (2)
C160.039 (3)0.048 (3)0.046 (3)0.011 (2)0.004 (2)0.003 (2)
C170.039 (3)0.050 (3)0.045 (2)0.005 (2)0.006 (2)0.008 (2)
C180.040 (2)0.036 (2)0.037 (2)0.011 (2)0.002 (2)0.005 (2)
C190.060 (3)0.062 (4)0.075 (4)0.015 (3)0.004 (3)0.020 (3)
C200.043 (3)0.044 (3)0.044 (3)0.010 (2)0.003 (2)0.004 (2)
O10.062 (2)0.0474 (18)0.0452 (18)0.0180 (18)0.0018 (16)0.0012 (16)
O20.064 (2)0.085 (3)0.0516 (19)0.008 (2)0.0189 (19)0.003 (2)
O30.0321 (17)0.078 (3)0.0503 (17)0.0125 (19)0.0014 (15)0.0176 (18)
O40.0439 (18)0.0333 (17)0.0505 (19)0.0012 (15)0.0005 (16)0.0057 (16)
O50.0347 (16)0.0341 (16)0.0346 (15)0.0039 (14)0.0004 (13)0.0058 (13)
O60.060 (2)0.0386 (19)0.0552 (19)0.0018 (18)0.0093 (17)0.0120 (17)
Geometric parameters (Å, º) top
C1—O11.445 (5)C11—H11A0.9700
C1—C21.458 (6)C11—H11B0.9700
C1—C91.490 (6)C12—C131.513 (5)
C1—C61.502 (6)C12—H12A0.9700
C2—O11.437 (5)C12—H12B0.9700
C2—C31.484 (6)C13—C141.498 (6)
C2—H20.9800C13—C181.515 (6)
C3—O21.197 (5)C13—C201.543 (6)
C3—C41.502 (6)C14—O51.444 (5)
C4—C51.545 (6)C14—C151.447 (6)
C4—H4A0.9700C14—C161.501 (6)
C4—H4B0.9700C15—O51.429 (5)
C5—C61.510 (6)C15—H150.9800
C5—H5A0.9700C16—C171.533 (6)
C5—H5B0.9700C16—H16A0.9700
C6—C71.503 (6)C16—H16B0.9700
C6—C191.533 (7)C17—C181.509 (6)
C7—O31.197 (4)C17—H17A0.9700
C7—C81.509 (5)C17—H17B0.9700
C8—C91.536 (6)C18—O61.207 (5)
C8—C101.540 (6)C19—H19A0.9600
C8—H80.9800C19—H19B0.9600
C9—H9A0.9700C19—H19C0.9600
C9—H9B0.9700C20—H20A0.9600
C10—O41.423 (5)C20—H20B0.9600
C10—C111.522 (5)C20—H20C0.9600
C10—C151.530 (5)O4—H40.8200
C11—C121.522 (5)
O1—C1—C259.3 (3)C12—C11—H11B108.5
O1—C1—C9115.4 (4)C10—C11—H11B108.5
C2—C1—C9129.0 (4)H11A—C11—H11B107.5
O1—C1—C6113.8 (4)C13—C12—C11111.0 (3)
C2—C1—C6120.2 (3)C13—C12—H12A109.4
C9—C1—C6108.1 (3)C11—C12—H12A109.4
O1—C2—C159.9 (3)C13—C12—H12B109.4
O1—C2—C3113.0 (4)C11—C12—H12B109.4
C1—C2—C3117.1 (4)H12A—C12—H12B108.0
O1—C2—H2117.9C14—C13—C12110.8 (3)
C1—C2—H2117.9C14—C13—C18100.1 (3)
C3—C2—H2117.9C12—C13—C18117.6 (3)
O2—C3—C2120.3 (4)C14—C13—C20111.1 (4)
O2—C3—C4121.0 (4)C12—C13—C20111.8 (4)
C2—C3—C4118.7 (4)C18—C13—C20104.8 (3)
C3—C4—C5116.9 (4)O5—C14—C1559.3 (2)
C3—C4—H4A108.1O5—C14—C13113.4 (3)
C5—C4—H4A108.1C15—C14—C13121.7 (4)
C3—C4—H4B108.1O5—C14—C16112.2 (3)
C5—C4—H4B108.1C15—C14—C16130.3 (4)
H4A—C4—H4B107.3C13—C14—C16106.8 (3)
C6—C5—C4111.3 (4)O5—C15—C1460.3 (3)
C6—C5—H5A109.4O5—C15—C10112.7 (3)
C4—C5—H5A109.4C14—C15—C10122.2 (4)
C6—C5—H5B109.4O5—C15—H15116.4
C4—C5—H5B109.4C14—C15—H15116.4
H5A—C5—H5B108.0C10—C15—H15116.4
C1—C6—C7101.1 (3)C14—C16—C17101.5 (3)
C1—C6—C5110.7 (4)C14—C16—H16A111.5
C7—C6—C5115.2 (4)C17—C16—H16A111.5
C1—C6—C19109.7 (4)C14—C16—H16B111.5
C7—C6—C19107.0 (4)C17—C16—H16B111.5
C5—C6—C19112.4 (4)H16A—C16—H16B109.3
O3—C7—C6124.4 (4)C18—C17—C16106.2 (3)
O3—C7—C8125.6 (4)C18—C17—H17A110.5
C6—C7—C8110.0 (3)C16—C17—H17A110.5
C7—C8—C9104.9 (3)C18—C17—H17B110.5
C7—C8—C10115.5 (3)C16—C17—H17B110.5
C9—C8—C10115.0 (3)H17A—C17—H17B108.7
C7—C8—H8107.0O6—C18—C17125.8 (4)
C9—C8—H8107.0O6—C18—C13126.1 (4)
C10—C8—H8107.0C17—C18—C13108.0 (4)
C1—C9—C8102.0 (3)C6—C19—H19A109.5
C1—C9—H9A111.4C6—C19—H19B109.5
C8—C9—H9A111.4H19A—C19—H19B109.5
C1—C9—H9B111.4C6—C19—H19C109.5
C8—C9—H9B111.4H19A—C19—H19C109.5
H9A—C9—H9B109.2H19B—C19—H19C109.5
O4—C10—C11111.4 (3)C13—C20—H20A109.5
O4—C10—C15105.0 (3)C13—C20—H20B109.5
C11—C10—C15112.0 (3)H20A—C20—H20B109.5
O4—C10—C8108.8 (3)C13—C20—H20C109.5
C11—C10—C8112.5 (3)H20A—C20—H20C109.5
C15—C10—C8106.8 (3)H20B—C20—H20C109.5
C12—C11—C10114.9 (3)C2—O1—C160.8 (3)
C12—C11—H11A108.5C10—O4—H4109.5
C10—C11—H11A108.5C15—O5—C1460.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O6i0.822.243.005 (4)156
C4—H4A···O6ii0.972.683.600 (6)159
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x+1/2, y+1, z1/2.
 

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