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The all-cis racemate of the title compound, C11H18O2, crystallizes in the chair-chair conformation that places the carboxyl group in an equatorial postion. The space group is centrosymmetric but the compound aggregates as dimers whose components are related by a C2 axis [O...O = 2.665 (3) Å and O—H...O = 177°]. In the crystal structure, one C—H...O=C close contact is found.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006410/su6176sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006410/su6176Isup2.hkl
Contains datablock I

CCDC reference: 270551

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.162
  • Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.77
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXP97 (Sheldrick, 1997a); software used to prepare material for publication: SHELXL97.

(1S*,4aR*,8aR*)-decahydronaphthalene-1-carboxylic acid top
Crystal data top
C11H18O2F(000) = 800
Mr = 182.25Dx = 1.168 Mg m3
Monoclinic, C2/cMelting point: 398 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 21.893 (9) ÅCell parameters from 24 reflections
b = 7.756 (3) Åθ = 3.5–8.9°
c = 13.187 (7) ŵ = 0.08 mm1
β = 112.23 (3)°T = 296 K
V = 2072.7 (16) Å3Parallelepiped, colourless
Z = 80.50 × 0.47 × 0.15 mm
Data collection top
Siemens P4
diffractometer
1247 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
2θ/θ scansh = 126
Absorption correction: analytical
(SHELXTL; Sheldrick, 1997b)
k = 91
Tmin = 0.957, Tmax = 0.987l = 1514
2324 measured reflections3 standard reflections every 97 reflections
1840 independent reflections intensity decay: variation <1.9%
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)] = 0.055H-atom parameters constrained
wR(F2) = 0.162 w = 1/[σ2(Fo2) + (0.0732P)2 + 1.5893P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
1840 reflectionsΔρmax = 0.49 e Å3
119 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0037 (10)
Special details top

Experimental. crystal mounted on glass fiber using cyanoacrylate cement

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
O10.00037 (8)0.2084 (3)0.62532 (14)0.0619 (6)
O20.08808 (8)0.2009 (3)0.77931 (14)0.0668 (6)
H20.06000.20410.80630.100*
C10.10653 (11)0.2284 (3)0.61498 (19)0.0429 (6)
H10.13940.13650.64280.051*
C20.07311 (13)0.2022 (4)0.4917 (2)0.0538 (7)
H2A0.05320.08850.47700.065*
H2B0.03830.28690.46160.065*
C30.12229 (15)0.2198 (4)0.4361 (2)0.0648 (8)
H3A0.15410.12660.45970.078*
H3B0.09920.21060.35740.078*
C4A0.19256 (11)0.4179 (3)0.5868 (2)0.0490 (6)
H4A0.22520.32550.61460.059*
C40.15837 (14)0.3915 (4)0.4633 (2)0.0580 (7)
H4B0.12710.48440.43250.070*
H4C0.19100.39600.43000.070*
C50.22985 (13)0.5889 (4)0.6168 (2)0.0623 (8)
H5A0.25820.58690.69390.075*
H5B0.25780.60080.57510.075*
C60.18456 (15)0.7443 (4)0.5951 (2)0.0646 (8)
H6A0.21080.84780.62080.077*
H6B0.16010.75590.51690.077*
C70.13669 (14)0.7256 (3)0.6527 (2)0.0606 (8)
H7A0.10590.82140.63250.073*
H7B0.16100.73030.73130.073*
C8A0.14411 (11)0.4015 (3)0.64530 (18)0.0398 (6)
H8A0.17040.39870.72420.048*
C80.09837 (11)0.5575 (3)0.6236 (2)0.0456 (6)
H8B0.06950.55940.54680.055*
H8C0.07100.54680.66650.055*
C90.05952 (12)0.2105 (3)0.67261 (19)0.0429 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0441 (10)0.0882 (15)0.0535 (11)0.0098 (10)0.0184 (8)0.0054 (10)
O20.0509 (11)0.1001 (16)0.0501 (11)0.0028 (11)0.0198 (8)0.0154 (10)
C10.0415 (13)0.0368 (13)0.0523 (14)0.0045 (11)0.0199 (11)0.0023 (10)
C20.0622 (16)0.0470 (15)0.0568 (15)0.0083 (13)0.0277 (13)0.0124 (12)
C30.082 (2)0.0630 (18)0.0611 (17)0.0021 (16)0.0397 (16)0.0138 (14)
C4A0.0398 (13)0.0515 (15)0.0586 (15)0.0055 (12)0.0221 (11)0.0077 (12)
C40.0631 (17)0.0625 (17)0.0610 (16)0.0043 (14)0.0376 (14)0.0054 (13)
C50.0483 (15)0.076 (2)0.0652 (17)0.0170 (15)0.0240 (13)0.0019 (15)
C60.0729 (19)0.0553 (18)0.0648 (17)0.0195 (15)0.0253 (15)0.0037 (13)
C70.0744 (19)0.0416 (15)0.0720 (18)0.0077 (14)0.0345 (15)0.0068 (13)
C8A0.0383 (12)0.0387 (13)0.0400 (12)0.0020 (10)0.0121 (10)0.0034 (10)
C80.0474 (13)0.0389 (13)0.0552 (14)0.0025 (11)0.0246 (11)0.0008 (11)
C90.0482 (14)0.0324 (12)0.0482 (13)0.0019 (11)0.0182 (11)0.0003 (11)
Geometric parameters (Å, º) top
O1—C91.220 (3)C4A—H4A0.9800
O2—C91.308 (3)C4—H4B0.9700
O2—H20.8200C4—H4C0.9700
C1—C91.499 (3)C5—C61.517 (4)
C1—C21.523 (3)C5—H5A0.9700
C1—C8A1.546 (3)C5—H5B0.9700
C1—H10.9800C6—C71.516 (4)
C2—C31.521 (4)C6—H6A0.9700
C2—H2A0.9700C6—H6B0.9700
C2—H2B0.9700C7—C81.519 (3)
C3—C41.520 (4)C7—H7A0.9700
C3—H3A0.9700C7—H7B0.9700
C3—H3B0.9700C8A—C81.527 (3)
C4A—C41.527 (4)C8A—H8A0.9800
C4A—C51.529 (4)C8—H8B0.9700
C4A—C8A1.535 (3)C8—H8C0.9700
C9—O2—H2109.5C6—C5—H5A108.9
C9—C1—C2112.6 (2)C4A—C5—H5A108.9
C9—C1—C8A110.44 (18)C6—C5—H5B108.9
C2—C1—C8A112.67 (19)C4A—C5—H5B108.9
C9—C1—H1106.9H5A—C5—H5B107.8
C2—C1—H1106.9C7—C6—C5110.8 (2)
C8A—C1—H1106.9C7—C6—H6A109.5
C3—C2—C1111.2 (2)C5—C6—H6A109.5
C3—C2—H2A109.4C7—C6—H6B109.5
C1—C2—H2A109.4C5—C6—H6B109.5
C3—C2—H2B109.4H6A—C6—H6B108.1
C1—C2—H2B109.4C6—C7—C8112.1 (2)
H2A—C2—H2B108.0C6—C7—H7A109.2
C4—C3—C2111.4 (2)C8—C7—H7A109.2
C4—C3—H3A109.4C6—C7—H7B109.2
C2—C3—H3A109.4C8—C7—H7B109.2
C4—C3—H3B109.4H7A—C7—H7B107.9
C2—C3—H3B109.4C8—C8A—C4A111.67 (19)
H3A—C3—H3B108.0C8—C8A—C1113.10 (18)
C4—C4A—C5113.0 (2)C4A—C8A—C1110.08 (19)
C4—C4A—C8A111.8 (2)C8—C8A—H8A107.2
C5—C4A—C8A110.1 (2)C4A—C8A—H8A107.2
C4—C4A—H4A107.2C1—C8A—H8A107.2
C5—C4A—H4A107.2C7—C8—C8A111.9 (2)
C8A—C4A—H4A107.2C7—C8—H8B109.2
C3—C4—C4A111.7 (2)C8A—C8—H8B109.2
C3—C4—H4B109.3C7—C8—H8C109.2
C4A—C4—H4B109.3C8A—C8—H8C109.2
C3—C4—H4C109.3H8B—C8—H8C107.9
C4A—C4—H4C109.3O1—C9—O2122.2 (2)
H4B—C4—H4C107.9O1—C9—C1123.6 (2)
C6—C5—C4A113.1 (2)O2—C9—C1114.2 (2)
C9—C1—C2—C3179.6 (2)C5—C4A—C8A—C1179.90 (19)
C8A—C1—C2—C354.7 (3)C9—C1—C8A—C854.8 (2)
C1—C2—C3—C455.1 (3)C2—C1—C8A—C872.1 (2)
C2—C3—C4—C4A55.8 (3)C9—C1—C8A—C4A179.49 (18)
C5—C4A—C4—C3179.5 (2)C2—C1—C8A—C4A53.6 (3)
C8A—C4A—C4—C355.5 (3)C6—C7—C8—C8A54.5 (3)
C4—C4A—C5—C671.4 (3)C4A—C8A—C8—C754.4 (3)
C8A—C4A—C5—C654.5 (3)C1—C8A—C8—C7179.2 (2)
C4A—C5—C6—C754.8 (3)C2—C1—C9—O113.1 (3)
C5—C6—C7—C854.0 (3)C8A—C1—C9—O1113.8 (3)
C4—C4A—C8A—C873.0 (3)C2—C1—C9—O2168.2 (2)
C5—C4A—C8A—C853.6 (3)C8A—C1—C9—O264.9 (3)
C4—C4A—C8A—C153.5 (3)
 

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