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The crystal structure determination of the title compound, C12H20O2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806056443/ym2046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806056443/ym2046Isup2.hkl
Contains datablock I

CCDC reference: 636848

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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.

(1R,5R,6S)-6-(2-Hydroxyethyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol top
Crystal data top
C12H20O2F(000) = 216
Mr = 196.28Dx = 1.099 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4218 reflections
a = 6.9388 (6) Åθ = 1.6–28.0°
b = 6.7185 (6) ŵ = 0.07 mm1
c = 12.9422 (11) ÅT = 295 K
β = 100.563 (2)°Block, colourless
V = 593.12 (9) Å30.38 × 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 tube1449 reflections with I > 2/s(I)
Graphite monochromatorRint = 0.017
ω scansθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001a)
h = 89
Tmin = 0.889, Tmax = 0.992k = 88
4218 measured reflectionsl = 1716
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-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 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
O10.3613 (2)0.1269 (3)0.56458 (11)0.0579 (4)
H110.27740.08770.51580.069*
O20.2962 (3)0.3104 (4)0.55797 (18)0.0955 (9)
H210.39380.24080.55610.115*
C10.3009 (3)0.0832 (3)0.66260 (15)0.0465 (4)
H10.19170.01140.64900.056*
C20.2259 (3)0.2780 (3)0.70185 (14)0.0437 (4)
H20.32840.37800.70090.052*
C30.2017 (3)0.2541 (3)0.81787 (14)0.0474 (4)
H30.11780.13780.82150.057*
C40.4030 (3)0.2085 (4)0.88542 (17)0.0619 (6)
H410.48150.32890.89340.074*
H420.38540.16680.95480.074*
C50.5100 (3)0.0498 (4)0.83840 (19)0.0602 (6)
H50.61500.01120.88180.072*
C60.4665 (3)0.0112 (3)0.73917 (18)0.0533 (5)
C70.0420 (3)0.3534 (4)0.62897 (15)0.0517 (5)
H710.01220.48580.65140.062*
H720.06970.36420.55840.062*
C80.1368 (3)0.2238 (4)0.62551 (18)0.0579 (5)
H810.11170.09200.60040.070*
H820.16670.21090.69550.070*
C90.1058 (3)0.4295 (4)0.86050 (16)0.0548 (5)
C100.0519 (4)0.4052 (5)0.9040 (2)0.0764 (8)
H1010.10780.51420.93160.092*
H1020.10640.27930.90680.092*
C110.1942 (5)0.6304 (4)0.8556 (2)0.0772 (8)
H1110.10400.72980.87090.116*
H1120.22170.65250.78650.116*
H1130.31370.63850.90630.116*
C120.5697 (4)0.1812 (4)0.6980 (2)0.0713 (7)
H1210.67390.22740.75190.107*
H1220.62310.13760.63840.107*
H1230.47850.28750.67720.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0555 (8)0.0716 (10)0.0482 (7)0.0111 (8)0.0136 (6)0.0049 (7)
O20.0482 (9)0.128 (2)0.1017 (14)0.0177 (11)0.0090 (9)0.0650 (15)
C10.0427 (9)0.0490 (10)0.0481 (9)0.0106 (8)0.0088 (7)0.0000 (8)
C20.0417 (8)0.0462 (9)0.0434 (8)0.0126 (7)0.0081 (7)0.0034 (7)
C30.0465 (9)0.0525 (10)0.0429 (8)0.0109 (8)0.0075 (7)0.0033 (8)
C40.0552 (12)0.0809 (16)0.0467 (9)0.0080 (12)0.0013 (8)0.0008 (10)
C50.0468 (10)0.0669 (14)0.0626 (12)0.0025 (10)0.0012 (8)0.0137 (11)
C60.0452 (9)0.0509 (11)0.0644 (11)0.0064 (9)0.0113 (8)0.0072 (10)
C70.0499 (10)0.0557 (11)0.0493 (9)0.0060 (10)0.0086 (8)0.0121 (9)
C80.0462 (10)0.0668 (13)0.0573 (10)0.0072 (10)0.0002 (8)0.0119 (10)
C90.0583 (12)0.0590 (12)0.0482 (9)0.0085 (10)0.0127 (8)0.0008 (8)
C100.0760 (17)0.0796 (18)0.0826 (16)0.0053 (14)0.0383 (14)0.0026 (15)
C110.095 (2)0.0612 (14)0.0811 (16)0.0208 (15)0.0310 (15)0.0142 (13)
C120.0675 (14)0.0579 (14)0.0909 (17)0.0042 (12)0.0210 (13)0.0065 (12)
Geometric parameters (Å, º) top
O1—C11.437 (2)C5—H50.9300
O1—H110.8200C6—C121.498 (4)
O2—C81.404 (3)C7—C81.509 (3)
O2—H210.8200C7—H710.9700
C1—C61.512 (3)C7—H720.9700
C1—C21.529 (3)C8—H810.9700
C1—H10.9800C8—H820.9700
C2—C71.527 (3)C9—C101.329 (3)
C2—C31.550 (2)C9—C111.489 (4)
C2—H20.9800C10—H1010.9300
C3—C91.507 (3)C10—H1020.9300
C3—C41.537 (3)C11—H1110.9600
C3—H30.9800C11—H1120.9600
C4—C51.491 (4)C11—H1130.9600
C4—H410.9700C12—H1210.9600
C4—H420.9700C12—H1220.9600
C5—C61.329 (4)C12—H1230.9600
C1—O1—H11109.5C12—C6—C1116.2 (2)
C8—O2—H21109.5C8—C7—C2114.59 (17)
O1—C1—C6110.77 (16)C8—C7—H71108.6
O1—C1—C2106.87 (15)C2—C7—H71108.6
C6—C1—C2113.90 (16)C8—C7—H72108.6
O1—C1—H1108.4C2—C7—H72108.6
C6—C1—H1108.4H71—C7—H72107.6
C2—C1—H1108.4O2—C8—C7109.2 (2)
C7—C2—C1112.04 (16)O2—C8—H81109.8
C7—C2—C3113.95 (16)C7—C8—H81109.8
C1—C2—C3109.70 (15)O2—C8—H82109.8
C7—C2—H2106.9C7—C8—H82109.8
C1—C2—H2106.9H81—C8—H82108.3
C3—C2—H2106.9C10—C9—C11120.4 (3)
C9—C3—C4111.33 (18)C10—C9—C3120.8 (2)
C9—C3—C2114.04 (17)C11—C9—C3118.75 (19)
C4—C3—C2108.84 (17)C9—C10—H101120.0
C9—C3—H3107.4C9—C10—H102120.0
C4—C3—H3107.4H101—C10—H102120.0
C2—C3—H3107.4C9—C11—H111109.5
C5—C4—C3112.25 (18)C9—C11—H112109.5
C5—C4—H41109.2H111—C11—H112109.5
C3—C4—H41109.2C9—C11—H113109.5
C5—C4—H42109.2H111—C11—H113109.5
C3—C4—H42109.2H112—C11—H113109.5
H41—C4—H42107.9C6—C12—H121109.5
C6—C5—C4125.0 (2)C6—C12—H122109.5
C6—C5—H5117.5H121—C12—H122109.5
C4—C5—H5117.5C6—C12—H123109.5
C5—C6—C12122.7 (2)H121—C12—H123109.5
C5—C6—C1121.0 (2)H122—C12—H123109.5
O1—C1—C2—C764.91 (18)C4—C5—C6—C11.4 (4)
C6—C1—C2—C7172.42 (16)O1—C1—C6—C5133.9 (2)
O1—C1—C2—C3167.48 (14)C2—C1—C6—C513.4 (3)
C6—C1—C2—C344.8 (2)O1—C1—C6—C1248.9 (2)
C7—C2—C3—C946.6 (2)C2—C1—C6—C12169.42 (17)
C1—C2—C3—C9173.13 (16)C1—C2—C7—C866.8 (2)
C7—C2—C3—C4171.56 (19)C3—C2—C7—C858.5 (3)
C1—C2—C3—C461.9 (2)C2—C7—C8—O2178.8 (2)
C9—C3—C4—C5173.83 (18)C4—C3—C9—C10110.6 (3)
C2—C3—C4—C547.3 (3)C2—C3—C9—C10125.7 (2)
C3—C4—C5—C616.6 (3)C4—C3—C9—C1167.8 (3)
C4—C5—C6—C12175.5 (2)C2—C3—C9—C1155.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O2i0.822.112.641 (3)123
O2—H21···O1ii0.821.892.693 (2)168
Symmetry codes: (i) x, y1/2, z+1; (ii) x1, y, z.
 

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