The crystal structure of the title compound, C
12H
16O
2, contains two crystallographically independent molecules in the asymmetric unit. The cyclohexane rings of these two molecules adopt chair conformations with the hydroxyl groups and benzene rings equatorially attached. The crystal structure is stabilized by O—H
O hydrogen bonds and weak C—H
π interactions involving the phenyl rings.
Supporting information
CCDC reference: 170789
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.078
- wR factor = 0.223
- Data-to-parameter ratio = 13.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ \P(PB)
H9B \P(PB)
PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ \P(PA)
H9D \P(PA)
PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ \P(PB)
H11B \P(PB)
PLAT_716 Alert C H...A Unknown or Inconsistent Label ........ \P(PA)
H11C \P(PA)
PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ \P(PB)
C9A \P(PB)
PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ \P(PA)
C9B \P(PA)
PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ \P(PB)
C11A \P(PB)
PLAT_717 Alert C D...A Unknown or Inconsistent Label ........ \P(PA)
C11B \P(PA)
PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ \P(PB)
C9A H9B \P(PB)
PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ \P(PA)
C9B H9D \P(PA)
PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ \P(PB)
C11A H11B \P(PB)
PLAT_718 Alert C D-H..A Unknown or Inconsistent label ........ \P(PA)
C11B H11C \P(PA)
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
12 Alert Level C = Please check
To a stirred suspension of magnesium turnings (0.75 g-atom) in dry THF (25 ml)
under a nitrogen atmosphere was added dropwise a solution of 2-bromoanisole
(3.8 ml, 0.03 M) in dry THF (15 ml). After the addition was complete,
the solution was cooled to 263 K (using an ice–salt mixture), and cuprous
iodide (0.29 g, 1.5 mmol) was added. The resulting mixture was then stirred
for a further 15 min, after which time cyclohexane oxide (2 ml, 0.02 M)
in dry THF (10 ml) was added dropwise. After completion of the reaction, it
was quenched with a saturated solution of ammonium sulfate (50 ml). The
reaction mixture was then extracted with ethyl acetate and the organic layer
was washed with water, then dried over anhydrous MgSO4. After removal of the
solvent, the residue was chromatographed over silica gel to afford
trans-2-(2-methoxyphenyl)cyclohexanol (4.1 g, 98%) as a viscous liquid
in 98% yield. It was then further demethylated with chlorotrimethylsilane
(2.17 g, 0.02 M) and sodium iodide (3 g, 0.02 M) using dry
acetonitrile as solvent, affording the title compound as a crystalline solid
(m.p. 367–369 K).
After checking their presence in the difference map, all the H atoms were placed
in geometrically calculated positions and a riding model was used for their
refinement. A rotating group refinement was used for the hydroxyl groups.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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 and PLATON (Spek, 1990).
trans-2-(2-hydroxyphenyl)-cyclohexanol
top
Crystal data top
C12H16O2 | Z = 4 |
Mr = 192.25 | F(000) = 416 |
Triclinic, P1 | Dx = 1.224 Mg m−3 |
a = 9.0290 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0804 (8) Å | Cell parameters from 2614 reflections |
c = 12.1751 (10) Å | θ = 1.8–28.4° |
α = 72.031 (2)° | µ = 0.08 mm−1 |
β = 81.913 (2)° | T = 293 K |
γ = 89.545 (2)° | Plate, colourless |
V = 1042.9 (1) Å3 | 0.48 × 0.40 × 0.14 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1965 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
Detector resolution: 8.33 pixels mm-1 | h = −10→10 |
ω scans | k = −11→11 |
5444 measured reflections | l = 0→14 |
3503 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.223 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.121P)2] where P = (Fo2 + 2Fc2)/3 |
3503 reflections | (Δ/σ)max < 0.001 |
257 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Crystal data top
C12H16O2 | γ = 89.545 (2)° |
Mr = 192.25 | V = 1042.9 (1) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.0290 (7) Å | Mo Kα radiation |
b = 10.0804 (8) Å | µ = 0.08 mm−1 |
c = 12.1751 (10) Å | T = 293 K |
α = 72.031 (2)° | 0.48 × 0.40 × 0.14 mm |
β = 81.913 (2)° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1965 reflections with I > 2σ(I) |
5444 measured reflections | Rint = 0.046 |
3503 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.223 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.29 e Å−3 |
3503 reflections | Δρmin = −0.32 e Å−3 |
257 parameters | |
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 | x | y | z | Uiso*/Ueq | |
O1A | 0.6366 (3) | 0.2862 (3) | 0.4524 (2) | 0.0573 (7) | |
H1A | 0.6805 | 0.3054 | 0.5005 | 0.086* | |
O2A | 0.3727 (3) | 0.1731 (3) | 0.4149 (2) | 0.0626 (8) | |
H2A | 0.4441 | 0.1967 | 0.4403 | 0.094* | |
C1A | 0.6423 (4) | 0.5366 (4) | 0.3718 (3) | 0.0532 (10) | |
H1B | 0.6646 | 0.5461 | 0.4413 | 0.064* | |
C2A | 0.6255 (4) | 0.6534 (4) | 0.2800 (4) | 0.0620 (11) | |
H2B | 0.6345 | 0.7420 | 0.2874 | 0.074* | |
C3A | 0.5957 (4) | 0.6374 (4) | 0.1780 (4) | 0.0638 (11) | |
H3A | 0.5866 | 0.7161 | 0.1151 | 0.077* | |
C4A | 0.5786 (4) | 0.5064 (4) | 0.1666 (3) | 0.0538 (10) | |
H4A | 0.5570 | 0.4986 | 0.0963 | 0.065* | |
C5A | 0.5929 (3) | 0.3863 (3) | 0.2580 (3) | 0.0402 (8) | |
C6A | 0.6258 (4) | 0.4048 (4) | 0.3610 (3) | 0.0431 (9) | |
C7A | 0.5765 (3) | 0.2407 (4) | 0.2488 (3) | 0.0412 (8) | |
H7A | 0.6449 | 0.1824 | 0.2974 | 0.049* | |
C8A | 0.6216 (4) | 0.2325 (4) | 0.1255 (3) | 0.0534 (10) | |
H8A | 0.5559 | 0.2891 | 0.0746 | 0.064* | |
H8B | 0.7229 | 0.2708 | 0.0966 | 0.064* | |
C9A | 0.6137 (5) | 0.0843 (4) | 0.1210 (4) | 0.0644 (11) | |
H9A | 0.6397 | 0.0842 | 0.0409 | 0.077* | |
H9B | 0.6853 | 0.0290 | 0.1665 | 0.077* | |
C10A | 0.4583 (4) | 0.0204 (4) | 0.1686 (3) | 0.0616 (11) | |
H10B | 0.4565 | −0.0761 | 0.1693 | 0.074* | |
H10A | 0.3884 | 0.0700 | 0.1181 | 0.074* | |
C11A | 0.4096 (4) | 0.0265 (4) | 0.2913 (3) | 0.0558 (10) | |
H11B | 0.3075 | −0.0104 | 0.3178 | 0.067* | |
H11A | 0.4730 | −0.0316 | 0.3434 | 0.067* | |
C12A | 0.4187 (4) | 0.1738 (4) | 0.2967 (3) | 0.0446 (9) | |
H12A | 0.3485 | 0.2293 | 0.2480 | 0.054* | |
O1B | 0.1221 (3) | 0.2119 (3) | 0.5432 (2) | 0.0573 (7) | |
H1C | 0.1905 | 0.1935 | 0.4990 | 0.086* | |
O2B | −0.1611 (3) | 0.3230 (3) | 0.5799 (2) | 0.0603 (8) | |
H2C | −0.0748 | 0.3256 | 0.5473 | 0.090* | |
C1B | 0.0957 (4) | −0.0388 (4) | 0.6229 (3) | 0.0520 (10) | |
H1D | 0.1458 | −0.0494 | 0.5541 | 0.062* | |
C2B | 0.0419 (4) | −0.1540 (4) | 0.7140 (3) | 0.0559 (10) | |
H2D | 0.0556 | −0.2425 | 0.7064 | 0.067* | |
C3B | −0.0315 (4) | −0.1404 (4) | 0.8156 (3) | 0.0526 (10) | |
H3B | −0.0687 | −0.2188 | 0.8769 | 0.063* | |
C4B | −0.0499 (4) | −0.0073 (4) | 0.8258 (3) | 0.0440 (9) | |
H4B | −0.0984 | 0.0017 | 0.8957 | 0.053* | |
C5B | 0.0009 (3) | 0.1113 (3) | 0.7366 (3) | 0.0383 (8) | |
C6B | 0.0753 (4) | 0.0941 (4) | 0.6331 (3) | 0.0434 (8) | |
C7B | −0.0191 (3) | 0.2574 (3) | 0.7458 (3) | 0.0381 (8) | |
H7B | 0.0673 | 0.3146 | 0.6969 | 0.046* | |
C8B | −0.0202 (4) | 0.2668 (4) | 0.8681 (3) | 0.0464 (9) | |
H8C | −0.1041 | 0.2106 | 0.9194 | 0.056* | |
H8D | 0.0709 | 0.2284 | 0.8969 | 0.056* | |
C9B | −0.0317 (4) | 0.4152 (4) | 0.8729 (3) | 0.0568 (10) | |
H9C | −0.0371 | 0.4149 | 0.9531 | 0.068* | |
H9D | 0.0569 | 0.4699 | 0.8281 | 0.068* | |
C10B | −0.1697 (4) | 0.4809 (4) | 0.8239 (3) | 0.0578 (10) | |
H10D | −0.2586 | 0.4327 | 0.8742 | 0.069* | |
H10C | −0.1714 | 0.5777 | 0.8223 | 0.069* | |
C11B | −0.1713 (4) | 0.4735 (4) | 0.7023 (3) | 0.0584 (11) | |
H11D | −0.0882 | 0.5304 | 0.6504 | 0.070* | |
H11C | −0.2632 | 0.5117 | 0.6752 | 0.070* | |
C12B | −0.1597 (4) | 0.3248 (4) | 0.6967 (3) | 0.0442 (9) | |
H12B | −0.2478 | 0.2703 | 0.7457 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0737 (18) | 0.0551 (16) | 0.0487 (15) | 0.0099 (13) | −0.0267 (13) | −0.0167 (12) |
O2A | 0.0514 (16) | 0.084 (2) | 0.0534 (16) | −0.0049 (15) | 0.0091 (13) | −0.0306 (14) |
C1A | 0.047 (2) | 0.061 (3) | 0.059 (2) | 0.0105 (18) | −0.0151 (18) | −0.026 (2) |
C2A | 0.057 (2) | 0.047 (2) | 0.086 (3) | 0.0159 (19) | −0.023 (2) | −0.022 (2) |
C3A | 0.064 (3) | 0.050 (3) | 0.072 (3) | 0.0168 (19) | −0.025 (2) | −0.005 (2) |
C4A | 0.053 (2) | 0.051 (2) | 0.057 (2) | 0.0111 (18) | −0.0214 (18) | −0.0098 (19) |
C5A | 0.0322 (17) | 0.047 (2) | 0.0402 (18) | 0.0092 (15) | −0.0073 (14) | −0.0104 (16) |
C6A | 0.0369 (18) | 0.046 (2) | 0.046 (2) | 0.0117 (15) | −0.0107 (15) | −0.0120 (17) |
C7A | 0.0308 (17) | 0.049 (2) | 0.0434 (19) | 0.0112 (15) | −0.0102 (14) | −0.0114 (16) |
C8A | 0.048 (2) | 0.063 (3) | 0.052 (2) | 0.0042 (18) | −0.0056 (17) | −0.0218 (19) |
C9A | 0.063 (3) | 0.073 (3) | 0.064 (3) | 0.013 (2) | −0.002 (2) | −0.034 (2) |
C10A | 0.064 (3) | 0.061 (3) | 0.069 (3) | 0.009 (2) | −0.019 (2) | −0.030 (2) |
C11A | 0.052 (2) | 0.048 (2) | 0.065 (2) | 0.0012 (17) | −0.0116 (19) | −0.0112 (19) |
C12A | 0.0367 (18) | 0.051 (2) | 0.044 (2) | 0.0091 (15) | −0.0070 (15) | −0.0114 (16) |
O1B | 0.0577 (17) | 0.0538 (16) | 0.0537 (16) | 0.0122 (12) | 0.0091 (12) | −0.0147 (13) |
O2B | 0.0558 (16) | 0.0805 (19) | 0.0523 (15) | 0.0283 (15) | −0.0255 (12) | −0.0247 (14) |
C1B | 0.046 (2) | 0.058 (3) | 0.055 (2) | 0.0201 (18) | −0.0082 (17) | −0.023 (2) |
C2B | 0.054 (2) | 0.044 (2) | 0.073 (3) | 0.0175 (18) | −0.017 (2) | −0.019 (2) |
C3B | 0.053 (2) | 0.043 (2) | 0.057 (2) | 0.0055 (17) | −0.0133 (18) | −0.0063 (18) |
C4B | 0.0410 (19) | 0.050 (2) | 0.0408 (19) | 0.0098 (16) | −0.0071 (15) | −0.0130 (17) |
C5B | 0.0267 (16) | 0.048 (2) | 0.0402 (18) | 0.0106 (14) | −0.0117 (14) | −0.0115 (16) |
C6B | 0.0397 (19) | 0.048 (2) | 0.043 (2) | 0.0134 (16) | −0.0076 (15) | −0.0137 (17) |
C7B | 0.0312 (16) | 0.043 (2) | 0.0385 (18) | 0.0096 (14) | −0.0048 (14) | −0.0104 (15) |
C8B | 0.049 (2) | 0.050 (2) | 0.045 (2) | 0.0102 (16) | −0.0159 (16) | −0.0175 (17) |
C9B | 0.065 (2) | 0.054 (2) | 0.059 (2) | 0.0090 (19) | −0.0157 (19) | −0.0253 (19) |
C10B | 0.059 (2) | 0.050 (2) | 0.068 (3) | 0.0161 (18) | −0.008 (2) | −0.0248 (19) |
C11B | 0.056 (2) | 0.051 (2) | 0.065 (3) | 0.0211 (18) | −0.0133 (19) | −0.0114 (19) |
C12B | 0.0385 (18) | 0.049 (2) | 0.043 (2) | 0.0126 (15) | −0.0100 (15) | −0.0092 (16) |
Geometric parameters (Å, º) top
O1A—C6A | 1.374 (4) | O1B—C6B | 1.365 (4) |
O1A—H1A | 0.820 | O1B—H1C | 0.820 |
O2A—C12A | 1.439 (4) | O2B—C12B | 1.429 (4) |
O2A—H2A | 0.820 | O2B—H2C | 0.820 |
C1A—C2A | 1.375 (5) | C1B—C2B | 1.370 (5) |
C1A—C6A | 1.386 (5) | C1B—C6B | 1.392 (5) |
C1A—H1B | 0.930 | C1B—H1D | 0.930 |
C2A—C3A | 1.363 (5) | C2B—C3B | 1.364 (5) |
C2A—H2B | 0.930 | C2B—H2D | 0.930 |
C3A—C4A | 1.382 (5) | C3B—C4B | 1.392 (5) |
C3A—H3A | 0.930 | C3B—H3B | 0.930 |
C4A—C5A | 1.389 (5) | C4B—C5B | 1.374 (4) |
C4A—H4A | 0.930 | C4B—H4B | 0.930 |
C5A—C6A | 1.395 (5) | C5B—C6B | 1.401 (4) |
C5A—C7A | 1.516 (5) | C5B—C7B | 1.519 (5) |
C7A—C8A | 1.527 (4) | C7B—C8B | 1.520 (4) |
C7A—C12A | 1.537 (5) | C7B—C12B | 1.543 (4) |
C7A—H7A | 0.980 | C7B—H7B | 0.980 |
C8A—C9A | 1.515 (6) | C8B—C9B | 1.516 (5) |
C8A—H8A | 0.970 | C8B—H8C | 0.970 |
C8A—H8B | 0.970 | C8B—H8D | 0.970 |
C9A—C10A | 1.509 (6) | C9B—C10B | 1.516 (5) |
C9A—H9A | 0.970 | C9B—H9C | 0.970 |
C9A—H9B | 0.970 | C9B—H9D | 0.970 |
C10A—C11A | 1.516 (5) | C10B—C11B | 1.507 (5) |
C10A—H10B | 0.970 | C10B—H10D | 0.970 |
C10A—H10A | 0.970 | C10B—H10C | 0.970 |
C11A—C12A | 1.509 (5) | C11B—C12B | 1.523 (5) |
C11A—H11B | 0.970 | C11B—H11D | 0.970 |
C11A—H11A | 0.970 | C11B—H11C | 0.970 |
C12A—H12A | 0.980 | C12B—H12B | 0.980 |
| | | |
C6A—O1A—H1A | 109.5 | C6B—O1B—H1C | 109.5 |
C12A—O2A—H2A | 109.5 | C12B—O2B—H2C | 109.5 |
C2A—C1A—C6A | 120.2 (4) | C2B—C1B—C6B | 120.0 (3) |
C2A—C1A—H1B | 119.9 | C2B—C1B—H1D | 120.0 |
C6A—C1A—H1B | 119.9 | C6B—C1B—H1D | 120.0 |
C3A—C2A—C1A | 119.0 (4) | C3B—C2B—C1B | 120.8 (4) |
C3A—C2A—H2B | 120.5 | C3B—C2B—H2D | 119.6 |
C1A—C2A—H2B | 120.5 | C1B—C2B—H2D | 119.6 |
C2A—C3A—C4A | 121.2 (4) | C2B—C3B—C4B | 118.9 (3) |
C2A—C3A—H3A | 119.4 | C2B—C3B—H3B | 120.5 |
C4A—C3A—H3A | 119.4 | C4B—C3B—H3B | 120.5 |
C3A—C4A—C5A | 121.3 (4) | C5B—C4B—C3B | 122.4 (3) |
C3A—C4A—H4A | 119.4 | C5B—C4B—H4B | 118.8 |
C5A—C4A—H4A | 119.4 | C3B—C4B—H4B | 118.8 |
C4A—C5A—C6A | 116.7 (3) | C4B—C5B—C6B | 117.4 (3) |
C4A—C5A—C7A | 123.0 (3) | C4B—C5B—C7B | 123.2 (3) |
C6A—C5A—C7A | 120.3 (3) | C6B—C5B—C7B | 119.4 (3) |
O1A—C6A—C1A | 121.5 (3) | O1B—C6B—C1B | 122.1 (3) |
O1A—C6A—C5A | 116.8 (3) | O1B—C6B—C5B | 117.5 (3) |
C1A—C6A—C5A | 121.6 (3) | C1B—C6B—C5B | 120.5 (3) |
C5A—C7A—C8A | 113.7 (3) | C5B—C7B—C8B | 114.3 (3) |
C5A—C7A—C12A | 113.4 (2) | C5B—C7B—C12B | 112.4 (3) |
C8A—C7A—C12A | 109.1 (3) | C8B—C7B—C12B | 109.6 (2) |
C5A—C7A—H7A | 106.7 | C5B—C7B—H7B | 106.7 |
C8A—C7A—H7A | 106.7 | C8B—C7B—H7B | 106.7 |
C12A—C7A—H7A | 106.7 | C12B—C7B—H7B | 106.7 |
C9A—C8A—C7A | 112.3 (3) | C9B—C8B—C7B | 112.9 (3) |
C9A—C8A—H8A | 109.1 | C9B—C8B—H8C | 109.0 |
C7A—C8A—H8A | 109.1 | C7B—C8B—H8C | 109.0 |
C9A—C8A—H8B | 109.1 | C9B—C8B—H8D | 109.0 |
C7A—C8A—H8B | 109.1 | C7B—C8B—H8D | 109.0 |
H8A—C8A—H8B | 107.9 | H8C—C8B—H8D | 107.8 |
C10A—C9A—C8A | 110.4 (3) | C10B—C9B—C8B | 110.5 (3) |
C10A—C9A—H9A | 109.6 | C10B—C9B—H9C | 109.5 |
C8A—C9A—H9A | 109.6 | C8B—C9B—H9C | 109.5 |
C10A—C9A—H9B | 109.6 | C10B—C9B—H9D | 109.5 |
C8A—C9A—H9B | 109.6 | C8B—C9B—H9D | 109.5 |
H9A—C9A—H9B | 108.1 | H9C—C9B—H9D | 108.1 |
C9A—C10A—C11A | 111.2 (3) | C11B—C10B—C9B | 111.2 (3) |
C9A—C10A—H10B | 109.4 | C11B—C10B—H10D | 109.4 |
C11A—C10A—H10B | 109.4 | C9B—C10B—H10D | 109.4 |
C9A—C10A—H10A | 109.4 | C11B—C10B—H10C | 109.4 |
C11A—C10A—H10A | 109.4 | C9B—C10B—H10C | 109.4 |
H10B—C10A—H10A | 108.0 | H10D—C10B—H10C | 108.0 |
C12A—C11A—C10A | 111.7 (3) | C10B—C11B—C12B | 112.4 (3) |
C12A—C11A—H11B | 109.3 | C10B—C11B—H11D | 109.1 |
C10A—C11A—H11B | 109.3 | C12B—C11B—H11D | 109.1 |
C12A—C11A—H11A | 109.3 | C10B—C11B—H11C | 109.1 |
C10A—C11A—H11A | 109.3 | C12B—C11B—H11C | 109.1 |
H11B—C11A—H11A | 107.9 | H11D—C11B—H11C | 107.8 |
O2A—C12A—C11A | 109.3 (3) | O2B—C12B—C11B | 110.4 (3) |
O2A—C12A—C7A | 111.6 (3) | O2B—C12B—C7B | 111.6 (3) |
C11A—C12A—C7A | 111.5 (3) | C11B—C12B—C7B | 110.7 (3) |
O2A—C12A—H12A | 108.1 | O2B—C12B—H12B | 108.0 |
C11A—C12A—H12A | 108.1 | C11B—C12B—H12B | 108.0 |
C7A—C12A—H12A | 108.1 | C7B—C12B—H12B | 108.0 |
| | | |
C6A—C1A—C2A—C3A | −1.3 (6) | C6B—C1B—C2B—C3B | −0.2 (5) |
C1A—C2A—C3A—C4A | 1.5 (6) | C1B—C2B—C3B—C4B | −0.6 (5) |
C2A—C3A—C4A—C5A | −0.8 (6) | C2B—C3B—C4B—C5B | 1.2 (5) |
C3A—C4A—C5A—C6A | −0.2 (5) | C3B—C4B—C5B—C6B | −0.9 (5) |
C3A—C4A—C5A—C7A | −179.4 (3) | C3B—C4B—C5B—C7B | 179.5 (3) |
C2A—C1A—C6A—O1A | −177.7 (3) | C2B—C1B—C6B—O1B | −177.5 (3) |
C2A—C1A—C6A—C5A | 0.3 (5) | C2B—C1B—C6B—C5B | 0.5 (5) |
C4A—C5A—C6A—O1A | 178.5 (3) | C4B—C5B—C6B—O1B | 178.2 (3) |
C7A—C5A—C6A—O1A | −2.3 (4) | C7B—C5B—C6B—O1B | −2.3 (4) |
C4A—C5A—C6A—C1A | 0.5 (5) | C4B—C5B—C6B—C1B | 0.1 (5) |
C7A—C5A—C6A—C1A | 179.7 (3) | C7B—C5B—C6B—C1B | 179.7 (3) |
C4A—C5A—C7A—C8A | 29.4 (4) | C4B—C5B—C7B—C8B | 31.0 (4) |
C6A—C5A—C7A—C8A | −149.7 (3) | C6B—C5B—C7B—C8B | −148.5 (3) |
C4A—C5A—C7A—C12A | −96.0 (4) | C4B—C5B—C7B—C12B | −94.7 (3) |
C6A—C5A—C7A—C12A | 84.9 (4) | C6B—C5B—C7B—C12B | 85.7 (3) |
C5A—C7A—C8A—C9A | 176.2 (3) | C5B—C7B—C8B—C9B | 176.8 (3) |
C12A—C7A—C8A—C9A | −56.2 (4) | C12B—C7B—C8B—C9B | −55.9 (4) |
C7A—C8A—C9A—C10A | 57.2 (4) | C7B—C8B—C9B—C10B | 56.4 (4) |
C8A—C9A—C10A—C11A | −55.8 (4) | C8B—C9B—C10B—C11B | −54.9 (4) |
C9A—C10A—C11A—C12A | 55.8 (4) | C9B—C10B—C11B—C12B | 55.8 (4) |
C10A—C11A—C12A—O2A | −179.5 (3) | C10B—C11B—C12B—O2B | −179.8 (3) |
C10A—C11A—C12A—C7A | −55.7 (4) | C10B—C11B—C12B—C7B | −55.6 (4) |
C5A—C7A—C12A—O2A | −54.7 (4) | C5B—C7B—C12B—O2B | −53.8 (4) |
C8A—C7A—C12A—O2A | 177.5 (3) | C8B—C7B—C12B—O2B | 177.9 (3) |
C5A—C7A—C12A—C11A | −177.2 (3) | C5B—C7B—C12B—C11B | −177.3 (3) |
C8A—C7A—C12A—C11A | 55.0 (4) | C8B—C7B—C12B—C11B | 54.4 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2Bi | 0.82 | 1.87 | 2.655 (4) | 159 |
O1B—H1C···O2A | 0.82 | 1.86 | 2.661 (4) | 167 |
O2A—H2A···O1A | 0.82 | 2.01 | 2.803 (4) | 163 |
O2B—H2C···O1B | 0.82 | 2.11 | 2.817 (4) | 144 |
C7A—H7A···O1A | 0.98 | 2.42 | 2.781 (4) | 101 |
C7B—H7B···O1B | 0.98 | 2.40 | 2.779 (4) | 103 |
C9A—H9B···π(PB)ii | 0.97 | 3.11 | 3.965 (5) | 148 |
C9B—H9D···π(PA)iii | 0.97 | 3.06 | 3.924 (4) | 149 |
C11A—H11B···π(PB)iv | 0.97 | 3.09 | 3.931 (4) | 146 |
C11B—H11C···π(PA)v | 0.97 | 3.11 | 3.930 (4) | 144 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z+1; (v) −x, −y+1, −z+1. |
Experimental details
Crystal data |
Chemical formula | C12H16O2 |
Mr | 192.25 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.0290 (7), 10.0804 (8), 12.1751 (10) |
α, β, γ (°) | 72.031 (2), 81.913 (2), 89.545 (2) |
V (Å3) | 1042.9 (1) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.48 × 0.40 × 0.14 |
|
Data collection |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5444, 3503, 1965 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.078, 0.223, 0.96 |
No. of reflections | 3503 |
No. of parameters | 257 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.32 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2Bi | 0.82 | 1.87 | 2.655 (4) | 159 |
O1B—H1C···O2A | 0.82 | 1.86 | 2.661 (4) | 167 |
O2A—H2A···O1A | 0.82 | 2.01 | 2.803 (4) | 163 |
O2B—H2C···O1B | 0.82 | 2.11 | 2.817 (4) | 144 |
C9A—H9B···π(PB)ii | 0.97 | 3.11 | 3.965 (5) | 148 |
C9B—H9D···π(PA)iii | 0.97 | 3.06 | 3.924 (4) | 149 |
C11A—H11B···π(PB)iv | 0.97 | 3.09 | 3.931 (4) | 146 |
C11B—H11C···π(PA)v | 0.97 | 3.11 | 3.930 (4) | 144 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z+1; (v) −x, −y+1, −z+1. |
Cyclohexanol and its derivatives have proved to be important tools in both biochemical and physiological studies of the cholimergin nerve terminal (Rogers et al., 1989). Also, many of the cyclohexanol derivatives exhibit good receptor properties against the inhibitor of acetylcholine storage by nerve terminal synaptic vesicles (Marshall & Parsons, 1987). The crystal structure determination of the title compound, (I), one of the above derivatives, was performed in order to elucidate its molecular conformation.
The asymmetric unit of (I) contains two crystallographically independent molecules linked by an O1B—H1C···O2A hydrogen bond, with their centroid at (0.252, 1/4, 0.497). The corresponding bond lengths and angles of these two molecules agree with each other and show normal values. The cyclohexane ring in both molecules adopts the chair conformation and the hydroxyl and phenyl groups are equatorially attached. An O—H···O intramolecular hydrogen bond is observed in one of the two molecules in the asymmetric unit (Table 1). In the solid state, the two independent molecules are alternately linked by O—H···O hydrogen bonds to form an infinite one-dimensional chain along the a direction. The crystal structure is further stabilized by a number of weak C—H···π interactions involving the phenyl rings of molecule A (πPA = centroid of C1A—C6A) and molecule B (πPB = centroid of C1B—C6B).