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The all-
cis racemate of the title compound, C
11H
18O
2, 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
CCDC reference: 270551
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (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
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.
(1
S*,4aR*,8aR*)-decahydronaphthalene-1-carboxylic acid
top
Crystal data top
C11H18O2 | F(000) = 800 |
Mr = 182.25 | Dx = 1.168 Mg m−3 |
Monoclinic, C2/c | Melting point: 398 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 21.893 (9) Å | Cell parameters from 24 reflections |
b = 7.756 (3) Å | θ = 3.5–8.9° |
c = 13.187 (7) Å | µ = 0.08 mm−1 |
β = 112.23 (3)° | T = 296 K |
V = 2072.7 (16) Å3 | Parallelepiped, colourless |
Z = 8 | 0.50 × 0.47 × 0.15 mm |
Data collection top
Siemens P4 diffractometer | 1247 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
2θ/θ scans | h = −1→26 |
Absorption correction: analytical (SHELXTL; Sheldrick, 1997b) | k = −9→1 |
Tmin = 0.957, Tmax = 0.987 | l = −15→14 |
2324 measured reflections | 3 standard reflections every 97 reflections |
1840 independent reflections | intensity decay: variation <1.9% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-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 reflections | Δρmax = 0.49 e Å−3 |
119 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | −0.00037 (8) | 0.2084 (3) | 0.62532 (14) | 0.0619 (6) | |
O2 | 0.08808 (8) | 0.2009 (3) | 0.77931 (14) | 0.0668 (6) | |
H2 | 0.0600 | 0.2041 | 0.8063 | 0.100* | |
C1 | 0.10653 (11) | 0.2284 (3) | 0.61498 (19) | 0.0429 (6) | |
H1 | 0.1394 | 0.1365 | 0.6428 | 0.051* | |
C2 | 0.07311 (13) | 0.2022 (4) | 0.4917 (2) | 0.0538 (7) | |
H2A | 0.0532 | 0.0885 | 0.4770 | 0.065* | |
H2B | 0.0383 | 0.2869 | 0.4616 | 0.065* | |
C3 | 0.12229 (15) | 0.2198 (4) | 0.4361 (2) | 0.0648 (8) | |
H3A | 0.1541 | 0.1266 | 0.4597 | 0.078* | |
H3B | 0.0992 | 0.2106 | 0.3574 | 0.078* | |
C4A | 0.19256 (11) | 0.4179 (3) | 0.5868 (2) | 0.0490 (6) | |
H4A | 0.2252 | 0.3255 | 0.6146 | 0.059* | |
C4 | 0.15837 (14) | 0.3915 (4) | 0.4633 (2) | 0.0580 (7) | |
H4B | 0.1271 | 0.4844 | 0.4325 | 0.070* | |
H4C | 0.1910 | 0.3960 | 0.4300 | 0.070* | |
C5 | 0.22985 (13) | 0.5889 (4) | 0.6168 (2) | 0.0623 (8) | |
H5A | 0.2582 | 0.5869 | 0.6939 | 0.075* | |
H5B | 0.2578 | 0.6008 | 0.5751 | 0.075* | |
C6 | 0.18456 (15) | 0.7443 (4) | 0.5951 (2) | 0.0646 (8) | |
H6A | 0.2108 | 0.8478 | 0.6208 | 0.077* | |
H6B | 0.1601 | 0.7559 | 0.5169 | 0.077* | |
C7 | 0.13669 (14) | 0.7256 (3) | 0.6527 (2) | 0.0606 (8) | |
H7A | 0.1059 | 0.8214 | 0.6325 | 0.073* | |
H7B | 0.1610 | 0.7303 | 0.7313 | 0.073* | |
C8A | 0.14411 (11) | 0.4015 (3) | 0.64530 (18) | 0.0398 (6) | |
H8A | 0.1704 | 0.3987 | 0.7242 | 0.048* | |
C8 | 0.09837 (11) | 0.5575 (3) | 0.6236 (2) | 0.0456 (6) | |
H8B | 0.0695 | 0.5594 | 0.5468 | 0.055* | |
H8C | 0.0710 | 0.5468 | 0.6665 | 0.055* | |
C9 | 0.05952 (12) | 0.2105 (3) | 0.67261 (19) | 0.0429 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0441 (10) | 0.0882 (15) | 0.0535 (11) | −0.0098 (10) | 0.0184 (8) | −0.0054 (10) |
O2 | 0.0509 (11) | 0.1001 (16) | 0.0501 (11) | 0.0028 (11) | 0.0198 (8) | 0.0154 (10) |
C1 | 0.0415 (13) | 0.0368 (13) | 0.0523 (14) | 0.0045 (11) | 0.0199 (11) | 0.0023 (10) |
C2 | 0.0622 (16) | 0.0470 (15) | 0.0568 (15) | −0.0083 (13) | 0.0277 (13) | −0.0124 (12) |
C3 | 0.082 (2) | 0.0630 (18) | 0.0611 (17) | −0.0021 (16) | 0.0397 (16) | −0.0138 (14) |
C4A | 0.0398 (13) | 0.0515 (15) | 0.0586 (15) | 0.0055 (12) | 0.0221 (11) | 0.0077 (12) |
C4 | 0.0631 (17) | 0.0625 (17) | 0.0610 (16) | −0.0043 (14) | 0.0376 (14) | −0.0054 (13) |
C5 | 0.0483 (15) | 0.076 (2) | 0.0652 (17) | −0.0170 (15) | 0.0240 (13) | 0.0019 (15) |
C6 | 0.0729 (19) | 0.0553 (18) | 0.0648 (17) | −0.0195 (15) | 0.0253 (15) | −0.0037 (13) |
C7 | 0.0744 (19) | 0.0416 (15) | 0.0720 (18) | −0.0077 (14) | 0.0345 (15) | −0.0068 (13) |
C8A | 0.0383 (12) | 0.0387 (13) | 0.0400 (12) | 0.0020 (10) | 0.0121 (10) | 0.0034 (10) |
C8 | 0.0474 (13) | 0.0389 (13) | 0.0552 (14) | 0.0025 (11) | 0.0246 (11) | 0.0008 (11) |
C9 | 0.0482 (14) | 0.0324 (12) | 0.0482 (13) | −0.0019 (11) | 0.0182 (11) | −0.0003 (11) |
Geometric parameters (Å, º) top
O1—C9 | 1.220 (3) | C4A—H4A | 0.9800 |
O2—C9 | 1.308 (3) | C4—H4B | 0.9700 |
O2—H2 | 0.8200 | C4—H4C | 0.9700 |
C1—C9 | 1.499 (3) | C5—C6 | 1.517 (4) |
C1—C2 | 1.523 (3) | C5—H5A | 0.9700 |
C1—C8A | 1.546 (3) | C5—H5B | 0.9700 |
C1—H1 | 0.9800 | C6—C7 | 1.516 (4) |
C2—C3 | 1.521 (4) | C6—H6A | 0.9700 |
C2—H2A | 0.9700 | C6—H6B | 0.9700 |
C2—H2B | 0.9700 | C7—C8 | 1.519 (3) |
C3—C4 | 1.520 (4) | C7—H7A | 0.9700 |
C3—H3A | 0.9700 | C7—H7B | 0.9700 |
C3—H3B | 0.9700 | C8A—C8 | 1.527 (3) |
C4A—C4 | 1.527 (4) | C8A—H8A | 0.9800 |
C4A—C5 | 1.529 (4) | C8—H8B | 0.9700 |
C4A—C8A | 1.535 (3) | C8—H8C | 0.9700 |
| | | |
C9—O2—H2 | 109.5 | C6—C5—H5A | 108.9 |
C9—C1—C2 | 112.6 (2) | C4A—C5—H5A | 108.9 |
C9—C1—C8A | 110.44 (18) | C6—C5—H5B | 108.9 |
C2—C1—C8A | 112.67 (19) | C4A—C5—H5B | 108.9 |
C9—C1—H1 | 106.9 | H5A—C5—H5B | 107.8 |
C2—C1—H1 | 106.9 | C7—C6—C5 | 110.8 (2) |
C8A—C1—H1 | 106.9 | C7—C6—H6A | 109.5 |
C3—C2—C1 | 111.2 (2) | C5—C6—H6A | 109.5 |
C3—C2—H2A | 109.4 | C7—C6—H6B | 109.5 |
C1—C2—H2A | 109.4 | C5—C6—H6B | 109.5 |
C3—C2—H2B | 109.4 | H6A—C6—H6B | 108.1 |
C1—C2—H2B | 109.4 | C6—C7—C8 | 112.1 (2) |
H2A—C2—H2B | 108.0 | C6—C7—H7A | 109.2 |
C4—C3—C2 | 111.4 (2) | C8—C7—H7A | 109.2 |
C4—C3—H3A | 109.4 | C6—C7—H7B | 109.2 |
C2—C3—H3A | 109.4 | C8—C7—H7B | 109.2 |
C4—C3—H3B | 109.4 | H7A—C7—H7B | 107.9 |
C2—C3—H3B | 109.4 | C8—C8A—C4A | 111.67 (19) |
H3A—C3—H3B | 108.0 | C8—C8A—C1 | 113.10 (18) |
C4—C4A—C5 | 113.0 (2) | C4A—C8A—C1 | 110.08 (19) |
C4—C4A—C8A | 111.8 (2) | C8—C8A—H8A | 107.2 |
C5—C4A—C8A | 110.1 (2) | C4A—C8A—H8A | 107.2 |
C4—C4A—H4A | 107.2 | C1—C8A—H8A | 107.2 |
C5—C4A—H4A | 107.2 | C7—C8—C8A | 111.9 (2) |
C8A—C4A—H4A | 107.2 | C7—C8—H8B | 109.2 |
C3—C4—C4A | 111.7 (2) | C8A—C8—H8B | 109.2 |
C3—C4—H4B | 109.3 | C7—C8—H8C | 109.2 |
C4A—C4—H4B | 109.3 | C8A—C8—H8C | 109.2 |
C3—C4—H4C | 109.3 | H8B—C8—H8C | 107.9 |
C4A—C4—H4C | 109.3 | O1—C9—O2 | 122.2 (2) |
H4B—C4—H4C | 107.9 | O1—C9—C1 | 123.6 (2) |
C6—C5—C4A | 113.1 (2) | O2—C9—C1 | 114.2 (2) |
| | | |
C9—C1—C2—C3 | −179.6 (2) | C5—C4A—C8A—C1 | −179.90 (19) |
C8A—C1—C2—C3 | 54.7 (3) | C9—C1—C8A—C8 | −54.8 (2) |
C1—C2—C3—C4 | −55.1 (3) | C2—C1—C8A—C8 | 72.1 (2) |
C2—C3—C4—C4A | 55.8 (3) | C9—C1—C8A—C4A | 179.49 (18) |
C5—C4A—C4—C3 | 179.5 (2) | C2—C1—C8A—C4A | −53.6 (3) |
C8A—C4A—C4—C3 | −55.5 (3) | C6—C7—C8—C8A | 54.5 (3) |
C4—C4A—C5—C6 | 71.4 (3) | C4A—C8A—C8—C7 | −54.4 (3) |
C8A—C4A—C5—C6 | −54.5 (3) | C1—C8A—C8—C7 | −179.2 (2) |
C4A—C5—C6—C7 | 54.8 (3) | C2—C1—C9—O1 | −13.1 (3) |
C5—C6—C7—C8 | −54.0 (3) | C8A—C1—C9—O1 | 113.8 (3) |
C4—C4A—C8A—C8 | −73.0 (3) | C2—C1—C9—O2 | 168.2 (2) |
C5—C4A—C8A—C8 | 53.6 (3) | C8A—C1—C9—O2 | −64.9 (3) |
C4—C4A—C8A—C1 | 53.5 (3) | | |
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