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The crystal structure of the title compound, C
11H
12O, a substrate for gold-catalysed cycloisomerization reactions [Hoffmann-Röder & Krause (2001).
Org. Lett.
3, 2537–2538], contains two molecules in the asymmetric unit. There are two intermolecular O—H
O hydrogen bonds in the crystal structure and a chain of molecules is formed along the
c axis
via these hydrogen bonds.
Supporting information
CCDC reference: 298702
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.011 Å
- R factor = 0.039
- wR factor = 0.084
- Data-to-parameter ratio = 8.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 32 Perc.
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C11 H12 O
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 25.45
From the CIF: _reflns_number_total 1832
Count of symmetry unique reflns 1867
Completeness (_total/calc) 98.13%
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
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
missing. This is required for a full paper submission (but is
optional for an electronic paper).
0 ALERT level A = Data missing that is essential or data in wrong format
1 ALERT level G = General alerts. Data that may be required is missing
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).
2-Methyl-4-phenylbuta-2,3-dien-1-ol
top
Crystal data top
C11H12O | F(000) = 688 |
Mr = 160.21 | Dx = 1.138 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 17261 reflections |
a = 24.379 (6) Å | θ = 3.1–25.1° |
b = 9.601 (2) Å | µ = 0.07 mm−1 |
c = 7.991 (3) Å | T = 173 K |
V = 1870.4 (9) Å3 | Needle, colourless |
Z = 8 | 0.15 × 0.08 × 0.08 mm |
Data collection top
Nonius KappaCCD diffractometer | 578 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 25.5°, θmin = 3.1° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −29→29 |
341 frames via ω–rotation (Δω=1°) and two times 80 s per frame
(four sets at different κ–angles) scans | k = −11→11 |
17261 measured reflections | l = −9→9 |
1832 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H-atom parameters constrained |
S = 1.00 | w = [exp(4.2(sinθ/λ)2)]/[σ2(Fo2)] |
1832 reflections | (Δ/σ)max < 0.001 |
221 parameters | Δρmax = 0.11 e Å−3 |
1 restraint | Δρmin = −0.11 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. 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 | 0.01022 (16) | −0.6427 (4) | −0.0840 (6) | 0.0752 (12) | |
H1 | 0.0239 | −0.6100 | 0.0041 | 0.113* | |
O1' | 0.04989 (14) | −0.4811 (3) | 0.1676 (6) | 0.0680 (11) | |
H1' | 0.0278 | −0.4302 | 0.2204 | 0.102* | |
C1 | 0.1463 (3) | −0.4429 (7) | −0.3628 (10) | 0.0604 (19) | |
C2 | 0.1491 (3) | −0.3067 (8) | −0.4280 (9) | 0.073 (3) | |
H2 | 0.1221 | −0.2768 | −0.5058 | 0.088* | |
C3 | 0.1901 (3) | −0.2160 (7) | −0.3816 (12) | 0.080 (3) | |
H3 | 0.1916 | −0.1257 | −0.4298 | 0.096* | |
C4 | 0.2292 (3) | −0.2557 (9) | −0.2649 (11) | 0.082 (3) | |
H4 | 0.2570 | −0.1921 | −0.2318 | 0.098* | |
C5 | 0.2277 (3) | −0.3879 (9) | −0.1968 (9) | 0.075 (3) | |
H5 | 0.2545 | −0.4160 | −0.1172 | 0.090* | |
C6 | 0.1859 (3) | −0.4808 (8) | −0.2469 (9) | 0.070 (2) | |
H6 | 0.1850 | −0.5716 | −0.2000 | 0.084* | |
C7 | 0.1015 (3) | −0.5389 (7) | −0.4103 (10) | 0.069 (2) | |
H7 | 0.0794 | −0.5126 | −0.5030 | 0.083* | |
C8 | 0.0895 (3) | −0.6551 (7) | −0.3376 (11) | 0.063 (2) | |
C9 | 0.0756 (3) | −0.7686 (8) | −0.2635 (9) | 0.063 (2) | |
C10 | 0.0343 (3) | −0.7743 (6) | −0.1191 (10) | 0.075 (2) | |
H10A | 0.0050 | −0.8415 | −0.1474 | 0.090* | |
H10B | 0.0531 | −0.8087 | −0.0173 | 0.090* | |
C11 | 0.0960 (3) | −0.9133 (6) | −0.3159 (11) | 0.088 (3) | |
H11A | 0.0656 | −0.9666 | −0.3638 | 0.132* | |
H11B | 0.1105 | −0.9624 | −0.2178 | 0.132* | |
H11C | 0.1252 | −0.9034 | −0.3996 | 0.132* | |
C1' | 0.1446 (3) | 0.0675 (7) | 0.1558 (11) | 0.063 (2) | |
C2' | 0.1458 (3) | 0.1997 (8) | 0.2218 (9) | 0.073 (3) | |
H2' | 0.1179 | 0.2293 | 0.2970 | 0.087* | |
C3' | 0.1883 (3) | 0.2906 (8) | 0.1776 (12) | 0.084 (3) | |
H3' | 0.1892 | 0.3827 | 0.2209 | 0.101* | |
C4' | 0.2288 (3) | 0.2451 (10) | 0.0708 (11) | 0.080 (3) | |
H4' | 0.2581 | 0.3057 | 0.0412 | 0.096* | |
C5' | 0.2271 (3) | 0.1123 (10) | 0.0070 (9) | 0.076 (3) | |
H5' | 0.2554 | 0.0824 | −0.0663 | 0.091* | |
C6' | 0.1856 (3) | 0.0220 (7) | 0.0466 (9) | 0.065 (2) | |
H6' | 0.1847 | −0.0693 | 0.0009 | 0.078* | |
C7' | 0.0984 (3) | −0.0256 (7) | 0.1990 (10) | 0.073 (2) | |
H7' | 0.0766 | −0.0007 | 0.2929 | 0.088* | |
C8' | 0.0845 (3) | −0.1437 (8) | 0.1159 (11) | 0.072 (2) | |
C9' | 0.0702 (3) | −0.2593 (8) | 0.0383 (10) | 0.073 (3) | |
C10' | 0.0922 (3) | −0.3971 (6) | 0.0973 (10) | 0.071 (2) | |
H10C | 0.1091 | −0.4468 | 0.0018 | 0.085* | |
H10D | 0.1211 | −0.3810 | 0.1824 | 0.085* | |
C11' | 0.0305 (3) | −0.2568 (7) | −0.1073 (9) | 0.081 (2) | |
H11D | 0.0151 | −0.1630 | −0.1190 | 0.121* | |
H11E | 0.0008 | −0.3235 | −0.0868 | 0.121* | |
H11F | 0.0499 | −0.2823 | −0.2103 | 0.121* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.073 (3) | 0.081 (3) | 0.071 (3) | 0.003 (2) | 0.002 (2) | −0.008 (3) |
O1' | 0.063 (2) | 0.068 (3) | 0.073 (3) | 0.001 (2) | 0.013 (2) | −0.001 (2) |
C1 | 0.055 (4) | 0.065 (5) | 0.062 (6) | 0.006 (4) | 0.009 (5) | 0.004 (5) |
C2 | 0.062 (5) | 0.079 (6) | 0.078 (7) | 0.013 (4) | 0.008 (4) | 0.011 (5) |
C3 | 0.080 (6) | 0.059 (5) | 0.100 (8) | −0.008 (5) | 0.021 (6) | −0.003 (5) |
C4 | 0.066 (6) | 0.077 (8) | 0.102 (9) | −0.013 (5) | 0.003 (5) | −0.011 (5) |
C5 | 0.067 (6) | 0.079 (8) | 0.078 (7) | 0.005 (5) | −0.002 (4) | −0.012 (5) |
C6 | 0.054 (5) | 0.085 (6) | 0.072 (6) | 0.007 (5) | 0.003 (4) | 0.011 (5) |
C7 | 0.049 (4) | 0.072 (5) | 0.086 (7) | 0.007 (4) | −0.009 (4) | 0.001 (5) |
C8 | 0.062 (4) | 0.059 (5) | 0.067 (6) | −0.003 (4) | −0.008 (4) | 0.003 (5) |
C9 | 0.058 (5) | 0.077 (6) | 0.055 (6) | −0.003 (4) | −0.014 (4) | −0.001 (4) |
C10 | 0.067 (5) | 0.066 (5) | 0.091 (7) | −0.006 (4) | −0.014 (5) | −0.008 (5) |
C11 | 0.092 (5) | 0.067 (5) | 0.105 (7) | 0.010 (4) | −0.026 (6) | −0.002 (5) |
C1' | 0.059 (5) | 0.057 (5) | 0.075 (6) | −0.010 (4) | −0.012 (5) | 0.009 (5) |
C2' | 0.071 (5) | 0.055 (5) | 0.092 (8) | 0.000 (4) | −0.014 (4) | 0.000 (5) |
C3' | 0.095 (7) | 0.063 (6) | 0.094 (8) | 0.009 (5) | −0.037 (6) | −0.018 (6) |
C4' | 0.079 (6) | 0.076 (7) | 0.084 (8) | −0.013 (5) | −0.018 (5) | 0.010 (5) |
C5' | 0.067 (6) | 0.075 (7) | 0.085 (7) | −0.003 (5) | −0.007 (4) | −0.003 (5) |
C6' | 0.074 (6) | 0.052 (5) | 0.069 (6) | 0.002 (5) | −0.012 (4) | 0.013 (4) |
C7' | 0.071 (5) | 0.074 (5) | 0.076 (7) | 0.008 (5) | 0.001 (4) | 0.001 (5) |
C8' | 0.059 (5) | 0.083 (5) | 0.074 (6) | 0.014 (5) | 0.004 (5) | 0.005 (5) |
C9' | 0.060 (5) | 0.069 (6) | 0.088 (8) | −0.012 (4) | 0.017 (4) | −0.004 (5) |
C10' | 0.065 (5) | 0.067 (5) | 0.081 (6) | 0.005 (4) | −0.006 (5) | −0.005 (4) |
C11' | 0.062 (5) | 0.107 (6) | 0.072 (7) | −0.011 (4) | 0.002 (5) | −0.011 (6) |
Geometric parameters (Å, º) top
O1—C10 | 1.421 (6) | C11—H11B | 0.9800 |
O1—H1 | 0.8400 | C11—H11C | 0.9800 |
O1'—C10' | 1.425 (7) | C1'—C2' | 1.375 (9) |
O1'—H1' | 0.8400 | C1'—C6' | 1.397 (8) |
C1—C6 | 1.387 (8) | C1'—C7' | 1.478 (8) |
C1—C2 | 1.410 (8) | C2'—C3' | 1.400 (9) |
C1—C7 | 1.479 (8) | C2'—H2' | 0.9500 |
C2—C3 | 1.376 (8) | C3'—C4' | 1.377 (10) |
C2—H2 | 0.9500 | C3'—H3' | 0.9500 |
C3—C4 | 1.387 (10) | C4'—C5' | 1.374 (11) |
C3—H3 | 0.9500 | C4'—H4' | 0.9500 |
C4—C5 | 1.381 (10) | C5'—C6' | 1.371 (8) |
C4—H4 | 0.9500 | C5'—H5' | 0.9500 |
C5—C6 | 1.411 (9) | C6'—H6' | 0.9500 |
C5—H5 | 0.9500 | C7'—C8' | 1.357 (9) |
C6—H6 | 0.9500 | C7'—H7' | 0.9500 |
C7—C8 | 1.291 (9) | C8'—C9' | 1.318 (10) |
C7—H7 | 0.9500 | C9'—C10' | 1.504 (9) |
C8—C9 | 1.285 (9) | C9'—C11' | 1.513 (9) |
C9—C10 | 1.533 (9) | C10'—H10C | 0.9900 |
C9—C11 | 1.535 (8) | C10'—H10D | 0.9900 |
C10—H10A | 0.9900 | C11'—H11D | 0.9800 |
C10—H10B | 0.9900 | C11'—H11E | 0.9800 |
C11—H11A | 0.9800 | C11'—H11F | 0.9800 |
| | | |
C10—O1—H1 | 109.5 | H11B—C11—H11C | 109.5 |
C10'—O1'—H1' | 109.5 | C2'—C1'—C6' | 120.9 (6) |
C6—C1—C2 | 117.1 (7) | C2'—C1'—C7' | 119.0 (8) |
C6—C1—C7 | 121.5 (7) | C6'—C1'—C7' | 120.1 (7) |
C2—C1—C7 | 121.3 (7) | C1'—C2'—C3' | 119.6 (8) |
C3—C2—C1 | 121.5 (8) | C1'—C2'—H2' | 120.2 |
C3—C2—H2 | 119.2 | C3'—C2'—H2' | 120.2 |
C1—C2—H2 | 119.2 | C4'—C3'—C2' | 119.3 (8) |
C2—C3—C4 | 120.4 (8) | C4'—C3'—H3' | 120.3 |
C2—C3—H3 | 119.8 | C2'—C3'—H3' | 120.3 |
C4—C3—H3 | 119.8 | C5'—C4'—C3' | 120.2 (8) |
C5—C4—C3 | 120.0 (8) | C5'—C4'—H4' | 119.9 |
C5—C4—H4 | 120.0 | C3'—C4'—H4' | 119.9 |
C3—C4—H4 | 120.0 | C6'—C5'—C4' | 121.6 (8) |
C4—C5—C6 | 119.2 (7) | C6'—C5'—H5' | 119.2 |
C4—C5—H5 | 120.4 | C4'—C5'—H5' | 119.2 |
C6—C5—H5 | 120.4 | C5'—C6'—C1' | 118.4 (7) |
C1—C6—C5 | 121.8 (7) | C5'—C6'—H6' | 120.8 |
C1—C6—H6 | 119.1 | C1'—C6'—H6' | 120.8 |
C5—C6—H6 | 119.1 | C8'—C7'—C1' | 125.5 (8) |
C8—C7—C1 | 126.2 (7) | C8'—C7'—H7' | 117.2 |
C8—C7—H7 | 116.9 | C1'—C7'—H7' | 117.2 |
C1—C7—H7 | 116.9 | C9'—C8'—C7' | 178.6 (8) |
C9—C8—C7 | 177.5 (8) | C8'—C9'—C10' | 119.8 (8) |
C8—C9—C10 | 123.4 (7) | C8'—C9'—C11' | 121.2 (7) |
C8—C9—C11 | 123.8 (8) | C10'—C9'—C11' | 118.9 (7) |
C10—C9—C11 | 112.7 (6) | O1'—C10'—C9' | 111.2 (5) |
O1—C10—C9 | 112.8 (6) | O1'—C10'—H10C | 109.4 |
O1—C10—H10A | 109.0 | C9'—C10'—H10C | 109.4 |
C9—C10—H10A | 109.0 | O1'—C10'—H10D | 109.4 |
O1—C10—H10B | 109.0 | C9'—C10'—H10D | 109.4 |
C9—C10—H10B | 109.0 | H10C—C10'—H10D | 108.0 |
H10A—C10—H10B | 107.8 | C9'—C11'—H11D | 109.5 |
C9—C11—H11A | 109.5 | C9'—C11'—H11E | 109.5 |
C9—C11—H11B | 109.5 | H11D—C11'—H11E | 109.5 |
H11A—C11—H11B | 109.5 | C9'—C11'—H11F | 109.5 |
C9—C11—H11C | 109.5 | H11D—C11'—H11F | 109.5 |
H11A—C11—H11C | 109.5 | H11E—C11'—H11F | 109.5 |
| | | |
C6—C1—C2—C3 | 1.4 (11) | C6'—C1'—C2'—C3' | 0.8 (11) |
C7—C1—C2—C3 | 178.6 (7) | C7'—C1'—C2'—C3' | −177.9 (6) |
C1—C2—C3—C4 | −1.7 (12) | C1'—C2'—C3'—C4' | −1.2 (12) |
C2—C3—C4—C5 | 1.2 (11) | C2'—C3'—C4'—C5' | 0.7 (12) |
C3—C4—C5—C6 | −0.3 (11) | C3'—C4'—C5'—C6' | 0.1 (12) |
C2—C1—C6—C5 | −0.5 (10) | C4'—C5'—C6'—C1' | −0.5 (11) |
C7—C1—C6—C5 | −177.8 (7) | C2'—C1'—C6'—C5' | 0.1 (11) |
C4—C5—C6—C1 | 0.0 (11) | C7'—C1'—C6'—C5' | 178.7 (6) |
C6—C1—C7—C8 | 10.0 (12) | C2'—C1'—C7'—C8' | 163.6 (7) |
C2—C1—C7—C8 | −167.1 (8) | C6'—C1'—C7'—C8' | −15.1 (12) |
C8—C9—C10—O1 | 4.2 (10) | C8'—C9'—C10'—O1' | 112.0 (7) |
C11—C9—C10—O1 | −172.7 (5) | C11'—C9'—C10'—O1' | −66.4 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O1′ | 0.84 | 1.91 | 2.717 (6) | 162 |
O1′—H1′···O1i | 0.84 | 1.95 | 2.739 (6) | 157 |
Symmetry code: (i) −x, −y−1, z+1/2. |
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