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In the title compound, C15H22O5, the cyclo­hexane ring A adopts a screw-boat conformation and ring B adopts a chair conformation. The carboxyl­ate groups are in a synclinal orientation with respect to each other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020220/cf6125sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020220/cf6125Isup2.hkl
Contains datablock I

CCDC reference: 177232

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.056
  • wR factor = 0.112
  • Data-to-parameter ratio = 19.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.32 From the CIF: _reflns_number_total 3500 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3734 Completeness (_total/calc) 93.73% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

8a-Ethyl 2-methyl (4aR,8aS)-3-oxoperhydro-2,8a-naphthalenedicarboxylate top
Crystal data top
C15H22O5Z = 2
Mr = 282.33F(000) = 304
Triclinic, P1Dx = 1.252 Mg m3
a = 6.8206 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5663 (4) ÅCell parameters from 2709 reflections
c = 11.9330 (4) Åθ = 1.7–56.7°
α = 97.092 (1)°µ = 0.09 mm1
β = 97.502 (1)°T = 293 K
γ = 100.954 (2)°Block, colourless
V = 749.03 (5) Å30.46 × 0.34 × 0.30 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
1893 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 28.3°, θmin = 1.7°
Detector resolution: 8.33 pixels mm-1h = 98
ω scansk = 1212
5358 measured reflectionsl = 1510
3500 independent reflections
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)] = 0.056H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0937P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
3500 reflectionsΔρmax = 0.25 e Å3
182 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.091 (13)
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

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
O11.3459 (2)0.28831 (18)1.02963 (15)0.0825 (5)
H1A1.30670.23641.07540.124*
O21.0828 (3)0.13080 (17)1.12396 (14)0.0792 (5)
O30.7558 (2)0.12348 (16)1.06203 (12)0.0670 (5)
O41.0740 (2)0.19521 (16)0.65671 (15)0.0844 (6)
O50.76324 (19)0.08718 (13)0.67211 (12)0.0601 (4)
C11.1860 (3)0.3075 (2)0.95923 (17)0.0562 (5)
C21.2435 (3)0.4001 (2)0.87297 (19)0.0627 (6)
H2A1.30700.34780.81820.075*
H2B1.34280.48480.91100.075*
C31.0666 (3)0.4483 (2)0.80882 (17)0.0545 (5)
H3A1.02870.51950.86370.065*
C41.1222 (4)0.5267 (2)0.7093 (2)0.0694 (6)
H4A1.23180.60910.73810.083*
H4B1.16970.46240.65460.083*
C50.9449 (4)0.5772 (3)0.6495 (2)0.0767 (7)
H5A0.98330.61880.58350.092*
H5B0.90890.65150.70110.092*
C60.7613 (4)0.4524 (3)0.61102 (19)0.0717 (6)
H6A0.64800.48840.57640.086*
H6B0.79300.38220.55400.086*
C70.7037 (3)0.3805 (2)0.71191 (17)0.0571 (5)
H7A0.58900.30110.68510.068*
H7B0.66210.44940.76570.068*
C80.8776 (2)0.32333 (18)0.77428 (15)0.0457 (4)
C90.8170 (3)0.2714 (2)0.88401 (15)0.0511 (5)
H9A0.75500.34240.92320.061*
H9B0.71650.18220.86340.061*
C100.9913 (3)0.24683 (19)0.96480 (16)0.0501 (5)
C110.9530 (3)0.1627 (2)1.05664 (18)0.0577 (5)
C120.7031 (4)0.0451 (3)1.1534 (2)0.0839 (8)
H12A0.55870.02281.14890.126*
H12B0.76310.10301.22570.126*
H12C0.75250.04261.14650.126*
C130.9202 (3)0.1979 (2)0.69544 (16)0.0517 (5)
C140.7858 (4)0.0393 (2)0.5981 (2)0.0713 (7)
H14A0.90560.07150.62860.086*
H14B0.80060.01620.52230.086*
C150.6043 (4)0.1542 (2)0.5915 (3)0.0948 (9)
H15A0.61710.23860.54280.142*
H15B0.48650.12180.56080.142*
H15C0.59120.17690.66670.142*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0461 (9)0.0903 (12)0.1002 (12)0.0101 (8)0.0097 (8)0.0011 (9)
O20.0769 (11)0.0815 (11)0.0756 (10)0.0199 (9)0.0046 (9)0.0100 (9)
O30.0644 (10)0.0711 (10)0.0653 (9)0.0081 (7)0.0166 (7)0.0127 (7)
O40.0641 (10)0.0733 (11)0.1051 (13)0.0023 (8)0.0402 (9)0.0307 (9)
O50.0519 (8)0.0447 (8)0.0724 (9)0.0015 (6)0.0067 (7)0.0135 (6)
C10.0389 (10)0.0588 (12)0.0626 (12)0.0088 (8)0.0006 (9)0.0124 (10)
C20.0360 (10)0.0663 (13)0.0736 (14)0.0047 (9)0.0108 (10)0.0147 (11)
C30.0475 (11)0.0477 (11)0.0596 (11)0.0032 (8)0.0167 (9)0.0136 (9)
C40.0709 (15)0.0555 (12)0.0741 (14)0.0076 (10)0.0268 (12)0.0032 (11)
C50.0946 (19)0.0626 (14)0.0741 (15)0.0099 (13)0.0267 (14)0.0113 (12)
C60.0805 (16)0.0729 (15)0.0603 (13)0.0151 (12)0.0108 (12)0.0067 (11)
C70.0496 (11)0.0594 (12)0.0585 (11)0.0097 (9)0.0094 (9)0.0035 (9)
C80.0355 (9)0.0465 (10)0.0494 (10)0.0012 (7)0.0102 (8)0.0070 (8)
C90.0355 (9)0.0609 (11)0.0505 (10)0.0008 (8)0.0089 (8)0.0042 (9)
C100.0426 (10)0.0509 (10)0.0503 (10)0.0052 (8)0.0064 (8)0.0094 (8)
C110.0579 (13)0.0515 (11)0.0562 (12)0.0095 (9)0.0028 (10)0.0117 (9)
C120.102 (2)0.0722 (15)0.0770 (16)0.0047 (13)0.0263 (15)0.0188 (13)
C130.0470 (11)0.0494 (11)0.0532 (11)0.0027 (8)0.0113 (9)0.0048 (8)
C140.0773 (15)0.0489 (12)0.0766 (15)0.0098 (10)0.0005 (12)0.0152 (11)
C150.093 (2)0.0540 (14)0.116 (2)0.0007 (13)0.0132 (16)0.0144 (14)
Geometric parameters (Å, º) top
O1—C11.343 (2)C3—C81.554 (2)
O2—C111.225 (2)C4—C51.513 (3)
O3—C111.338 (3)C5—C61.533 (3)
O3—C121.443 (3)C6—C71.517 (3)
O4—C131.204 (2)C7—C81.542 (3)
O5—C131.328 (2)C8—C131.528 (2)
O5—C141.453 (2)C8—C91.535 (3)
C1—C101.358 (3)C9—C101.503 (3)
C1—C21.482 (3)C10—C111.459 (3)
C2—C31.520 (3)C14—C151.478 (3)
C3—C41.531 (3)
C11—O3—C12116.74 (18)C9—C8—C7109.68 (14)
C13—O5—C14116.89 (15)C13—C8—C3111.67 (14)
O1—C1—C10123.8 (2)C9—C8—C3107.99 (14)
O1—C1—C2113.08 (17)C7—C8—C3108.88 (15)
C10—C1—C2123.11 (18)C10—C9—C8113.72 (14)
C1—C2—C3113.84 (15)C1—C10—C11118.05 (18)
C2—C3—C4113.39 (16)C1—C10—C9121.87 (18)
C2—C3—C8111.77 (16)C11—C10—C9119.98 (16)
C4—C3—C8113.34 (16)O2—C11—O3121.9 (2)
C5—C4—C3112.15 (17)O2—C11—C10125.5 (2)
C4—C5—C6111.18 (19)O3—C11—C10112.62 (18)
C7—C6—C5110.60 (18)O4—C13—O5122.07 (17)
C6—C7—C8113.05 (17)O4—C13—C8126.22 (17)
C13—C8—C9109.62 (15)O5—C13—C8111.72 (15)
C13—C8—C7108.98 (14)O5—C14—C15108.54 (19)
O1—C1—C2—C3168.13 (15)O1—C1—C10—C113.6 (3)
C10—C1—C2—C312.8 (3)C2—C1—C10—C11177.40 (16)
C1—C2—C3—C4172.27 (15)O1—C1—C10—C9179.99 (16)
C1—C2—C3—C842.7 (2)C2—C1—C10—C91.0 (3)
C2—C3—C4—C5178.24 (16)C8—C9—C10—C119.9 (2)
C8—C3—C4—C552.9 (2)C8—C9—C10—C11163.79 (15)
C3—C4—C5—C654.3 (2)C12—O3—C11—O21.8 (3)
C4—C5—C6—C756.4 (3)C12—O3—C11—C10177.39 (16)
C5—C6—C7—C857.7 (2)C1—C10—C11—O26.9 (3)
C6—C7—C8—C1367.7 (2)C9—C10—C11—O2176.64 (17)
C6—C7—C8—C9172.29 (16)C1—C10—C11—O3172.26 (16)
C6—C7—C8—C354.3 (2)C9—C10—C11—O34.2 (2)
C2—C3—C8—C1360.7 (2)C14—O5—C13—O40.6 (3)
C4—C3—C8—C1368.9 (2)C14—O5—C13—C8179.72 (16)
C2—C3—C8—C959.89 (19)C9—C8—C13—O4124.3 (2)
C4—C3—C8—C9170.47 (15)C7—C8—C13—O4115.7 (2)
C2—C3—C8—C7178.92 (15)C3—C8—C13—O44.6 (3)
C4—C3—C8—C751.4 (2)C9—C8—C13—O556.1 (2)
C13—C8—C9—C1074.19 (18)C7—C8—C13—O563.9 (2)
C7—C8—C9—C10166.20 (14)C3—C8—C13—O5175.74 (16)
C3—C8—C9—C1047.7 (2)C13—O5—C14—C15174.71 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.821.862.584 (2)146
 

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