The crystal structure determination of the title compound, C
12H
20O
2, is part of a model study carried out to investigate the chemistry related to our ongoing efforts toward the total synthesis of the zoanthamine alkaloids. The cyclohexene ring adopts a half-chair conformation. In the crystal structure, the molecules are linked by intermolecular O—H
O hydrogen bonds between the hydroxyl groups of neighbouring molecules, forming columns parallel to the
b axis.
Supporting information
CCDC reference: 636848
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.134
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
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 27.99
From the CIF: _reflns_number_total 1536
Count of symmetry unique reflns 1547
Completeness (_total/calc) 99.29%
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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
3 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001b); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(1
R,5
R,6
S)-6-(2-Hydroxyethyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol
top
Crystal data top
C12H20O2 | F(000) = 216 |
Mr = 196.28 | Dx = 1.099 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 4218 reflections |
a = 6.9388 (6) Å | θ = 1.6–28.0° |
b = 6.7185 (6) Å | µ = 0.07 mm−1 |
c = 12.9422 (11) Å | T = 295 K |
β = 100.563 (2)° | Block, colourless |
V = 593.12 (9) Å3 | 0.38 × 0.33 × 0.24 mm |
Z = 2 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 1536 independent reflections |
Radiation source: normal-focus sealed tube | 1449 reflections with I > 2/s(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 28.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001a) | h = −8→9 |
Tmin = 0.889, Tmax = 0.992 | k = −8→8 |
4218 measured reflections | l = −17→16 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0904P)2 + 0.0286P] where P = (Fo2 + 2Fc2)/3 |
1536 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.17 e Å−3 |
1 restraint | Δρmin = −0.24 e Å−3 |
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. Friedel pairs were merged before refinement |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.3613 (2) | 0.1269 (3) | 0.56458 (11) | 0.0579 (4) | |
H11 | 0.2774 | 0.0877 | 0.5158 | 0.069* | |
O2 | −0.2962 (3) | 0.3104 (4) | 0.55797 (18) | 0.0955 (9) | |
H21 | −0.3938 | 0.2408 | 0.5561 | 0.115* | |
C1 | 0.3009 (3) | 0.0832 (3) | 0.66260 (15) | 0.0465 (4) | |
H1 | 0.1917 | −0.0114 | 0.6490 | 0.056* | |
C2 | 0.2259 (3) | 0.2780 (3) | 0.70185 (14) | 0.0437 (4) | |
H2 | 0.3284 | 0.3780 | 0.7009 | 0.052* | |
C3 | 0.2017 (3) | 0.2541 (3) | 0.81787 (14) | 0.0474 (4) | |
H3 | 0.1178 | 0.1378 | 0.8215 | 0.057* | |
C4 | 0.4030 (3) | 0.2085 (4) | 0.88542 (17) | 0.0619 (6) | |
H41 | 0.4815 | 0.3289 | 0.8934 | 0.074* | |
H42 | 0.3854 | 0.1668 | 0.9548 | 0.074* | |
C5 | 0.5100 (3) | 0.0498 (4) | 0.83840 (19) | 0.0602 (6) | |
H5 | 0.6150 | −0.0112 | 0.8818 | 0.072* | |
C6 | 0.4665 (3) | −0.0112 (3) | 0.73917 (18) | 0.0533 (5) | |
C7 | 0.0420 (3) | 0.3534 (4) | 0.62897 (15) | 0.0517 (5) | |
H71 | 0.0122 | 0.4858 | 0.6514 | 0.062* | |
H72 | 0.0697 | 0.3642 | 0.5584 | 0.062* | |
C8 | −0.1368 (3) | 0.2238 (4) | 0.62551 (18) | 0.0579 (5) | |
H81 | −0.1117 | 0.0920 | 0.6004 | 0.070* | |
H82 | −0.1667 | 0.2109 | 0.6955 | 0.070* | |
C9 | 0.1058 (3) | 0.4295 (4) | 0.86050 (16) | 0.0548 (5) | |
C10 | −0.0519 (4) | 0.4052 (5) | 0.9040 (2) | 0.0764 (8) | |
H101 | −0.1078 | 0.5142 | 0.9316 | 0.092* | |
H102 | −0.1064 | 0.2793 | 0.9068 | 0.092* | |
C11 | 0.1942 (5) | 0.6304 (4) | 0.8556 (2) | 0.0772 (8) | |
H111 | 0.1040 | 0.7298 | 0.8709 | 0.116* | |
H112 | 0.2217 | 0.6525 | 0.7865 | 0.116* | |
H113 | 0.3137 | 0.6385 | 0.9063 | 0.116* | |
C12 | 0.5697 (4) | −0.1812 (4) | 0.6980 (2) | 0.0713 (7) | |
H121 | 0.6739 | −0.2274 | 0.7519 | 0.107* | |
H122 | 0.6231 | −0.1376 | 0.6384 | 0.107* | |
H123 | 0.4785 | −0.2875 | 0.6772 | 0.107* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0555 (8) | 0.0716 (10) | 0.0482 (7) | −0.0111 (8) | 0.0136 (6) | −0.0049 (7) |
O2 | 0.0482 (9) | 0.128 (2) | 0.1017 (14) | −0.0177 (11) | −0.0090 (9) | 0.0650 (15) |
C1 | 0.0427 (9) | 0.0490 (10) | 0.0481 (9) | −0.0106 (8) | 0.0088 (7) | 0.0000 (8) |
C2 | 0.0417 (8) | 0.0462 (9) | 0.0434 (8) | −0.0126 (7) | 0.0081 (7) | 0.0034 (7) |
C3 | 0.0465 (9) | 0.0525 (10) | 0.0429 (8) | −0.0109 (8) | 0.0075 (7) | 0.0033 (8) |
C4 | 0.0552 (12) | 0.0809 (16) | 0.0467 (9) | −0.0080 (12) | 0.0013 (8) | −0.0008 (10) |
C5 | 0.0468 (10) | 0.0669 (14) | 0.0626 (12) | −0.0025 (10) | −0.0012 (8) | 0.0137 (11) |
C6 | 0.0452 (9) | 0.0509 (11) | 0.0644 (11) | −0.0064 (9) | 0.0113 (8) | 0.0072 (10) |
C7 | 0.0499 (10) | 0.0557 (11) | 0.0493 (9) | −0.0060 (10) | 0.0086 (8) | 0.0121 (9) |
C8 | 0.0462 (10) | 0.0668 (13) | 0.0573 (10) | −0.0072 (10) | 0.0002 (8) | 0.0119 (10) |
C9 | 0.0583 (12) | 0.0590 (12) | 0.0482 (9) | −0.0085 (10) | 0.0127 (8) | −0.0008 (8) |
C10 | 0.0760 (17) | 0.0796 (18) | 0.0826 (16) | −0.0053 (14) | 0.0383 (14) | −0.0026 (15) |
C11 | 0.095 (2) | 0.0612 (14) | 0.0811 (16) | −0.0208 (15) | 0.0310 (15) | −0.0142 (13) |
C12 | 0.0675 (14) | 0.0579 (14) | 0.0909 (17) | 0.0042 (12) | 0.0210 (13) | 0.0065 (12) |
Geometric parameters (Å, º) top
O1—C1 | 1.437 (2) | C5—H5 | 0.9300 |
O1—H11 | 0.8200 | C6—C12 | 1.498 (4) |
O2—C8 | 1.404 (3) | C7—C8 | 1.509 (3) |
O2—H21 | 0.8200 | C7—H71 | 0.9700 |
C1—C6 | 1.512 (3) | C7—H72 | 0.9700 |
C1—C2 | 1.529 (3) | C8—H81 | 0.9700 |
C1—H1 | 0.9800 | C8—H82 | 0.9700 |
C2—C7 | 1.527 (3) | C9—C10 | 1.329 (3) |
C2—C3 | 1.550 (2) | C9—C11 | 1.489 (4) |
C2—H2 | 0.9800 | C10—H101 | 0.9300 |
C3—C9 | 1.507 (3) | C10—H102 | 0.9300 |
C3—C4 | 1.537 (3) | C11—H111 | 0.9600 |
C3—H3 | 0.9800 | C11—H112 | 0.9600 |
C4—C5 | 1.491 (4) | C11—H113 | 0.9600 |
C4—H41 | 0.9700 | C12—H121 | 0.9600 |
C4—H42 | 0.9700 | C12—H122 | 0.9600 |
C5—C6 | 1.329 (4) | C12—H123 | 0.9600 |
| | | |
C1—O1—H11 | 109.5 | C12—C6—C1 | 116.2 (2) |
C8—O2—H21 | 109.5 | C8—C7—C2 | 114.59 (17) |
O1—C1—C6 | 110.77 (16) | C8—C7—H71 | 108.6 |
O1—C1—C2 | 106.87 (15) | C2—C7—H71 | 108.6 |
C6—C1—C2 | 113.90 (16) | C8—C7—H72 | 108.6 |
O1—C1—H1 | 108.4 | C2—C7—H72 | 108.6 |
C6—C1—H1 | 108.4 | H71—C7—H72 | 107.6 |
C2—C1—H1 | 108.4 | O2—C8—C7 | 109.2 (2) |
C7—C2—C1 | 112.04 (16) | O2—C8—H81 | 109.8 |
C7—C2—C3 | 113.95 (16) | C7—C8—H81 | 109.8 |
C1—C2—C3 | 109.70 (15) | O2—C8—H82 | 109.8 |
C7—C2—H2 | 106.9 | C7—C8—H82 | 109.8 |
C1—C2—H2 | 106.9 | H81—C8—H82 | 108.3 |
C3—C2—H2 | 106.9 | C10—C9—C11 | 120.4 (3) |
C9—C3—C4 | 111.33 (18) | C10—C9—C3 | 120.8 (2) |
C9—C3—C2 | 114.04 (17) | C11—C9—C3 | 118.75 (19) |
C4—C3—C2 | 108.84 (17) | C9—C10—H101 | 120.0 |
C9—C3—H3 | 107.4 | C9—C10—H102 | 120.0 |
C4—C3—H3 | 107.4 | H101—C10—H102 | 120.0 |
C2—C3—H3 | 107.4 | C9—C11—H111 | 109.5 |
C5—C4—C3 | 112.25 (18) | C9—C11—H112 | 109.5 |
C5—C4—H41 | 109.2 | H111—C11—H112 | 109.5 |
C3—C4—H41 | 109.2 | C9—C11—H113 | 109.5 |
C5—C4—H42 | 109.2 | H111—C11—H113 | 109.5 |
C3—C4—H42 | 109.2 | H112—C11—H113 | 109.5 |
H41—C4—H42 | 107.9 | C6—C12—H121 | 109.5 |
C6—C5—C4 | 125.0 (2) | C6—C12—H122 | 109.5 |
C6—C5—H5 | 117.5 | H121—C12—H122 | 109.5 |
C4—C5—H5 | 117.5 | C6—C12—H123 | 109.5 |
C5—C6—C12 | 122.7 (2) | H121—C12—H123 | 109.5 |
C5—C6—C1 | 121.0 (2) | H122—C12—H123 | 109.5 |
| | | |
O1—C1—C2—C7 | 64.91 (18) | C4—C5—C6—C1 | 1.4 (4) |
C6—C1—C2—C7 | −172.42 (16) | O1—C1—C6—C5 | 133.9 (2) |
O1—C1—C2—C3 | −167.48 (14) | C2—C1—C6—C5 | 13.4 (3) |
C6—C1—C2—C3 | −44.8 (2) | O1—C1—C6—C12 | −48.9 (2) |
C7—C2—C3—C9 | −46.6 (2) | C2—C1—C6—C12 | −169.42 (17) |
C1—C2—C3—C9 | −173.13 (16) | C1—C2—C7—C8 | 66.8 (2) |
C7—C2—C3—C4 | −171.56 (19) | C3—C2—C7—C8 | −58.5 (3) |
C1—C2—C3—C4 | 61.9 (2) | C2—C7—C8—O2 | 178.8 (2) |
C9—C3—C4—C5 | −173.83 (18) | C4—C3—C9—C10 | −110.6 (3) |
C2—C3—C4—C5 | −47.3 (3) | C2—C3—C9—C10 | 125.7 (2) |
C3—C4—C5—C6 | 16.6 (3) | C4—C3—C9—C11 | 67.8 (3) |
C4—C5—C6—C12 | −175.5 (2) | C2—C3—C9—C11 | −55.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11···O2i | 0.82 | 2.11 | 2.641 (3) | 123 |
O2—H21···O1ii | 0.82 | 1.89 | 2.693 (2) | 168 |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x−1, y, z. |