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ISSN: 2414-3146

(4S,5S,6R,E)-3,5-Di­methyl-6-vinyl­hept-2-ene-1,4,7-triol

aFakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
*Correspondence e-mail: hans.preut@tu-dortmund.de

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 22 April 2016; accepted 25 April 2016; online 29 April 2016)

The title compound, C11H20O3, was obtained in the course of the total syntheses of curvicollides A–C and features the same relative configuration for the central lactone moiety as that reported for the latter compounds. In the crystal, mol­ecules are linked via O—H⋯O hydrogen bonds: all of the OH groups act as donors as well as acceptors for these bonds, hence each mol­ecule is bound to six surrounding mol­ecules and a three-dimensional network is formed. The absolute structure was confirmed by refinement of the Flack parameter.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

As a key precursor in the total synthesis of curvicollides A–C we obtained the title compound (I) (Fig. 1[link]) through reductive cleavage of the benzyl ethers in (4S,5S,6R,E)-1-(benz­yloxy)-6-[(benz­yloxy)meth­yl]-3,5-di­methyl­octa-2,7-dien-4-ol, (II). Background to curvicollides is given by Che et al., (2004[Che, Y., Gloer, J. B. & Wicklow, D. T. (2004). Org. Lett. 6, 1249-1252.]) and synthetic studies of curvicollides are described by Körner & Hiersemann (2007[Körner, M. & Hiersemann, M. (2007). Org. Lett. 9, 4979-4982.]). The stereotriade in the title compound was generated from an enanti­oselective transformation employing the catalytic asymmetric Gosteli–Claisen rearrangement followed by a diastereoselective reduction. The absolute configuration was determined based on the previously described stereochemical course of the catalytic asymmetric Gosteli–Claisen rearrangement using a modified Evans–Cu{(S,S)-tert-butyl-box}–Lewis acid catalyst. For the synthesis of the Evans–Cu{(S,S)-tert-butyl-box} catalyst, see: Evans et al. (1999[Evans, D. A., Miller, S. J., Lectka, T. & von Matt, P. (1999). J. Am. Chem. Soc. 121, 7559-7573.]) and Jaschinski & Hiersemann (2012[Jaschinski, T. & Hiersemann, M. (2012). Org. Lett. 14, 4114-4117.]).

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.

In the crystal, mol­ecules are linked via O—H⋯O hydrogen bonds (Table 1[link]): all of the OH groups act as donors as well as acceptors for these bonds, hence each mol­ecule is bound to six surrounding mol­ecules and a three-dimensional network is formed Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯O1i 0.91 (2) 1.77 (2) 2.6681 (16) 166 (3)
O3—H3⋯O2ii 0.89 (2) 1.83 (2) 2.6983 (16) 166 (2)
O1—H1⋯O3iii 0.92 (2) 1.83 (2) 2.7458 (17) 172 (2)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) x+1, y, z; (iii) x, y-1, z.
[Figure 2]
Figure 2
The mol­ecular structure of the title compound showing the six hydrogen bonds around the mol­ecule. H atoms on C atoms have been omitted for clarity. [Symmetry codes: (A) x, y − 1, z; (B) [{1\over 2}] + x, y − [{1\over 2}], 1 − z; (C) x − 1, y, z; (D) x − [{1\over 2}], [{1\over 2}] − y, 1 − z; (E) x, 1 + y, z; (F) 1 + x, y, z.]

Synthesis and crystallization

The synthesis of the title compound was carried out under the conditions for reductive cleavage of benzyl ethers (Liu et al., 1997[Liu, H., Yip, J. & Shia, K. S. (1997). Tetrahedron Lett. 38, 2253-2256.]). To a solution of naphthalene (C10H8, M = 128.17 g mol−1, 69.5 g, 542.35 mmol, 1.499 equiv.) in THF (300 ml), small pieces of freshly cut lithium metal (Li, M = 6.94 g mol−1, 2.51 g, 361.67 mmol, 1 equiv.) were added at room temperature. Within 30 minutes, the colour of the reaction mixture turned to dark green. The reaction mixture was stirred for a further 3 h in order to completely dissolve the metal. The mixture was then transferred within 45 minutes via a canula to a solution of the benzyl­ether (II) (C25H32O3, M = 380.52 g mol−1, 5.51 g, 14.48 mmol, 1 equiv) in THF (65 ml) at 195 K. After stirring for 2 h, saturated aqueous ammonium chloride solution (100 ml) was added and the mixture was allowed to reach room temperature. The phases were separ­ated and the aqueous layer was extracted with ethyl acetate (3 × 100 ml). The combined organic phases were dried (MgSO4), filtered and concentrated under reduced pressure. Purification of the residue by flash chromatography (cyclo­hexa­ne/ethyl acetate 10/1 to 2/1 to ethyl acetate) delivered the title compound (I) (C11H20O3, M = 200.27 g mol−1, 2.58 g, 12.88 mmol, 88%) as a pale yellow solid. Single crystals of (I) were obtained by adding n-pentane (6 ml) to a solution of (I) in diethyl ether (0.4 ml). Crystallization was completed by slow evaporation of the solvent over three days and yielded (I) as colourless needles. Rf 0.28 (ethyl acetate); m.p. 335.5–337.5 K; 1H NMR (CDCl3, 300 MHz) δ 0.85 (d, J = 7.3 Hz, 3 H, 5-CH3) 1.59 (s, 3 H, 3-CH3) 1.96 (quind, J = 7.0, 1.8 Hz, 1 H, 5-H) 2.36–2.48 (m, 1 H, 6-H) 3.43–3.69 (m, 2 H, 7-H2) 3.84 (d, J = 6.6 Hz, 1 H, 4-H) 3.95 (br s, 1 H, OH) 4.11 (dd, J = 12.8, 5.9 Hz, 1 H, 1-Ha) 4.22 (dd, J = 12.8, 7.3 Hz, 1 H, 1-Hb) 4.94–5.15 (m, 3 H, CH=CH2, OH) 5.18 (br s, 1 H, OH) 5.58 (t, J = 6.4 Hz, 1H, 2-H) 5.77 (ddd, J = 17.2, 10.4, 8.2 Hz, 1H, CH=CH2); 13C NMR (CDCl3, 75 MHz) δ 12.38 (3-CH3) 13.91 (5-CH3) 38.65 (CH-5) 46.54 (CH-6) 58.86 (CH2-1) 62.73 (CH2-7) 78.59 (CH-4) 116.48 (CH=CH2) 125.75 (CH-2) 137.99 (CH=CH2) 139.12 (C-3); IR (cm−1): 3334 (br s), 2967 (s), 2880 (s), 1667 (w), 1634 (w), 1455 (m), 1383 (m) 1003 (s) 918 (w), 756 (s), 666 (w); HRMS (ESI) calculated for C11H20O3Na ([M + Na]+): 223.13047, found 223.12963. Analysis calculated for C11H20O3: C, 65.97; H, 10.07; found: C, 65.7; H, 9.9; [α]D20 = +46 (c 1, CHCl3).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C11H20O3
Mr 200.27
Crystal system, space group Orthorhombic, P212121
Temperature (K) 100
a, b, c (Å) 5.8932 (9), 7.1714 (9), 27.347 (4)
V3) 1155.7 (3)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.66
Crystal size (mm) 0.22 × 0.10 × 0.05
 
Data collection
Diffractometer Bruker D8 VENTURE CCD
Absorption correction Multi-scan (SADABS; Bruker, 2012[Bruker (2012). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
No. of measured, independent and observed [I > 2σ(I)] reflections 7921, 2189, 2154
Rint 0.025
(sin θ/λ)max−1) 0.610
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.080, 1.10
No. of reflections 2189
No. of parameters 141
No. of restraints 3
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.19, −0.17
Absolute structure Flack x determined using 862 quotients [(I+)−(I)]/[(I+)+(I)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.])
Absolute structure parameter 0.06 (4)
Computer programs: SMART and SAINT (Bruker, 2012[Bruker (2012). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXD, SHELXTL-Plus and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Experimental top

The synthesis of the title compound was carried out under the conditions for reductive cleavage of benzyl ethers (Liu et al., 1997). To a solution of naphthalene (C10H8, M = 128.17 g mol-1, 69.5 g, 542.35 mmol, 1.499 equiv.) in THF (300 ml), small pieces of freshly cut lithium metal (Li, M = 6.94 g mol-1, 2.51 g, 361.67 mmol, 1 equiv.) were added at room temperature. Within 30 minutes, the colour of the reaction mixture turned to dark green. The reaction mixture was stirred for a further 3 h in order to completely dissolve the metal. The mixture was then transferred within 45 minutes via a canula to a solution of the benzylether (II) (C25H32O3, M = 380.52 g mol-1, 5.51 g, 14.48 mmol, 1 equiv) in THF (65 ml) at 195 K. After stirring for 2 h, saturated aqueous ammonium chloride solution (100 ml) was added and the mixture was allowed to reach room temperature. The phases were separated and the aqueous layer was extracted with ethyl acetate (3 × 100 ml). The combined organic phases were dried (MgSO4), filtered and concentrated under reduced pressure. Purification of the residue by flash chromatography (cyclohexane/ethyl acetate 10/1 to 2/1 to ethyl acetate) delivered the title compound (I) (C11H20O3, M = 200.27 g mol-1, 2.58 g, 12.88 mmol, 88%) as a pale yellow solid. Single crystals of (I) were obtained by adding n-pentane (6 ml) to a solution of (I) in diethyl ether (0.4 ml). Crystallization was completed by slow evaporation of the solvent over three days and yielded (I) as colourless needles. Rf 0.28 (ethyl acetate); m.p. 335.5–337.5 K; 1H NMR (CDCl3, 300 MHz) δ 0.85 (d, J = 7.3 Hz, 3 H, 5-CH3) 1.59 (s, 3 H, 3-CH3) 1.96 (quind, J = 7.0, 1.8 Hz, 1 H, 5-H) 2.36–2.48 (m, 1 H, 6-H) 3.43–3.69 (m, 2 H, 7-H2) 3.84 (d, J = 6.6 Hz, 1 H, 4-H) 3.95 (br s, 1 H, OH) 4.11 (dd, J = 12.8, 5.9 Hz, 1 H, 1-Ha) 4.22 (dd, J = 12.8, 7.3 Hz, 1 H, 1-Hb) 4.94–5.15 (m, 3 H, CHCH2, OH) 5.18 (br s, 1 H, OH) 5.58 (t, J = 6.4 Hz, 1H, 2-H) 5.77 (ddd, J = 17.2, 10.4, 8.2 Hz, 1H, CHCH2); 13C NMR (CDCl3, 75 MHz) δ 12.38 (3-CH3) 13.91 (5-CH3) 38.65 (CH-5) 46.54 (CH-6) 58.86 (CH2-1) 62.73 (CH2-7) 78.59 (CH-4) 116.48 (CHCH2) 125.75 (CH-2) 137.99 (CHCH2) 139.12 (C-3); IR (cm-1): 3334 (br s), 2967 (s), 2880 (s), 1667 (w), 1634 (w), 1455 (m), 1383 (m) 1003 (s) 918 (w), 756 (s), 666 (w); HRMS (ESI) calculated for C11H20O3Na ([M + Na]+): 223.13047, found 223.12963. Analysis calculated for C11H20O3: C, 65.97; H, 10.07; found: C, 65.7; H, 9.9; [α]D20 = +46 (c 1, CHCl3).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2.

Structure description top

As a key precursor in the total synthesis of curvicollides A–C we obtained the title compound (I) (Fig. 1) through reductive cleavage of the benzyl ethers in (4S,5S,6R,E)-1-(benzyloxy)-6-[(benzyloxy)methyl]-3,5-dimethylocta-2,7-dien-4-ol, (II). Background to curvicollides is given by Che et al., (2004) and synthetic studies of curvicollides are described by Körner & Hiersemann (2007). The stereotriade in the title compound was generated from an enantioselective transformation employing the catalytic asymmetric Gosteli–Claisen rearrangement followed by a diastereoselective reduction. The absolute configuration was determined based on the previously described stereochemical course of the catalytic asymmetric Gosteli–Claisen rearrangement using a modified Evans–Cu{(S,S)-tert-butyl-box}–Lewis acid catalyst. For the synthesis of the Evans–Cu{(S,S)-tert-butyl-box} catalyst, see: Evans et al. (1999) and Jaschinski & Hiersemann (2012).

In the crystal, molecules are linked via O—H···O hydrogen bonds (Table 1): all of the OH groups act as donors as well as acceptors for these bonds, hence each molecule is bound to six surrounding molecules and a three-dimensional network is formed Fig. 2).

Computing details top

Data collection: SMART (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The molecular structure of the title compound showing the six hydrogen bonds around the molecule. H atoms on C atoms have been omitted for clarity. [Symmetry codes: (A) x, y - 1, z; (B) 1/2 + x, y - 1/2, 1 - z; (C) x - 1, y, z; (D) x - 1/2, 1/2 - y, 1 - z; (E) x, 1 + y, z; (F) 1 + x, y, z.]
(4S,5S,6R,E)-3,5-Dimethyl-6-vinylhept-2-ene-1,4,7-triol top
Crystal data top
C11H20O3Dx = 1.151 Mg m3
Mr = 200.27Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 7854 reflections
a = 5.8932 (9) Åθ = 3.2–70.2°
b = 7.1714 (9) ŵ = 0.66 mm1
c = 27.347 (4) ÅT = 100 K
V = 1155.7 (3) Å3Plate, colourless-yellow
Z = 40.22 × 0.10 × 0.05 mm
F(000) = 440
Data collection top
Bruker D8 VENTURE CCD
diffractometer
2189 independent reflections
Radiation source: microfocus sealed X-ray tube2154 reflections with I > 2σ(I)
Detector resolution: 7.9 pixels mm-1Rint = 0.025
ω and φ scansθmax = 70.2°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 77
k = 88
7921 measured reflectionsl = 2733
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0446P)2 + 0.1631P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
2189 reflectionsΔρmax = 0.19 e Å3
141 parametersΔρmin = 0.17 e Å3
3 restraintsAbsolute structure: Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (4)
Crystal data top
C11H20O3V = 1155.7 (3) Å3
Mr = 200.27Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 5.8932 (9) ŵ = 0.66 mm1
b = 7.1714 (9) ÅT = 100 K
c = 27.347 (4) Å0.22 × 0.10 × 0.05 mm
Data collection top
Bruker D8 VENTURE CCD
diffractometer
2189 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
2154 reflections with I > 2σ(I)
Rint = 0.025
7921 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.080Δρmax = 0.19 e Å3
S = 1.10Δρmin = 0.17 e Å3
2189 reflectionsAbsolute structure: Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
141 parametersAbsolute structure parameter: 0.06 (4)
3 restraints
Special details top

Experimental. A total of 1956 frames were collected. The total exposure time was 43.62 hours. The frames were integrated with the Bruker SAINT software package using a narrow-frame algorithm. The integration of the data yielded a total of 7921 reflections to maximum angle of 70.22° (0.82 Å resolution), of which 2189 were independent (completeness 99.5%).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4533 (2)0.10535 (18)0.51945 (4)0.0343 (3)
H10.510 (4)0.150 (3)0.5486 (7)0.046 (6)*
O20.0463 (2)0.60420 (16)0.57604 (4)0.0248 (3)
H20.038 (5)0.598 (4)0.5427 (7)0.060 (8)*
O30.63256 (19)0.73206 (19)0.60174 (4)0.0297 (3)
H30.771 (4)0.686 (4)0.5986 (9)0.053 (7)*
C10.2461 (3)0.0061 (2)0.52644 (6)0.0286 (4)
H1A0.14790.07690.54920.034*
H1B0.16560.00390.49480.034*
C20.2851 (3)0.1850 (2)0.54652 (5)0.0221 (3)
H2A0.41860.24710.53590.026*
C30.1529 (2)0.2779 (2)0.57773 (5)0.0207 (3)
C40.2178 (2)0.4751 (2)0.59199 (5)0.0195 (3)
H40.36420.50770.57560.023*
C50.2444 (3)0.5057 (2)0.64742 (5)0.0201 (3)
H50.09040.48870.66210.024*
C60.3197 (3)0.7081 (2)0.65976 (5)0.0216 (3)
H60.23090.79490.63850.026*
C70.2623 (3)0.7525 (2)0.71240 (5)0.0275 (4)
H70.33630.68210.73710.033*
C80.1175 (3)0.8815 (3)0.72652 (6)0.0362 (4)
H8A0.04010.95480.70290.043*
H8B0.09030.90130.76040.043*
C90.0663 (3)0.2043 (3)0.59807 (6)0.0302 (4)
H9A0.06270.21130.63390.045*
H9B0.08630.07430.58790.045*
H9C0.19280.27940.58570.045*
C100.3971 (3)0.3580 (2)0.67028 (6)0.0291 (4)
H10A0.32640.23500.66670.044*
H10B0.41830.38560.70510.044*
H10C0.54470.35830.65380.044*
C110.5714 (3)0.7499 (3)0.65208 (5)0.0275 (3)
H11A0.60480.87820.66330.033*
H11B0.66340.66260.67190.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0504 (7)0.0307 (6)0.0219 (5)0.0196 (6)0.0061 (5)0.0026 (5)
O20.0329 (6)0.0235 (6)0.0181 (5)0.0067 (5)0.0054 (4)0.0018 (4)
O30.0228 (5)0.0433 (7)0.0229 (5)0.0026 (5)0.0006 (4)0.0048 (5)
C10.0370 (9)0.0214 (7)0.0274 (8)0.0039 (7)0.0020 (7)0.0028 (6)
C20.0257 (7)0.0207 (7)0.0198 (6)0.0006 (6)0.0006 (6)0.0013 (6)
C30.0227 (7)0.0212 (7)0.0183 (6)0.0001 (6)0.0008 (5)0.0011 (6)
C40.0208 (7)0.0205 (7)0.0173 (6)0.0018 (6)0.0013 (5)0.0002 (5)
C50.0207 (7)0.0232 (7)0.0164 (7)0.0014 (6)0.0012 (5)0.0002 (5)
C60.0244 (7)0.0238 (8)0.0165 (6)0.0001 (6)0.0016 (5)0.0018 (6)
C70.0331 (8)0.0311 (8)0.0182 (7)0.0041 (8)0.0017 (6)0.0040 (6)
C80.0409 (9)0.0404 (10)0.0272 (8)0.0006 (9)0.0044 (7)0.0115 (7)
C90.0279 (8)0.0274 (8)0.0352 (8)0.0061 (7)0.0073 (7)0.0055 (7)
C100.0343 (9)0.0284 (8)0.0245 (7)0.0073 (8)0.0053 (7)0.0009 (6)
C110.0274 (7)0.0343 (9)0.0207 (7)0.0060 (7)0.0032 (6)0.0008 (6)
Geometric parameters (Å, º) top
O1—C11.426 (2)C5—H51.0000
O1—H10.922 (19)C6—C71.5125 (19)
O2—C41.4380 (18)C6—C111.528 (2)
O2—H20.914 (19)C6—H61.0000
O3—C111.4288 (18)C7—C81.317 (3)
O3—H30.89 (2)C7—H70.9500
C1—C21.494 (2)C8—H8A0.9500
C1—H1A0.9900C8—H8B0.9500
C1—H1B0.9900C9—H9A0.9800
C2—C31.334 (2)C9—H9B0.9800
C2—H2A0.9500C9—H9C0.9800
C3—C91.502 (2)C10—H10A0.9800
C3—C41.516 (2)C10—H10B0.9800
C4—C51.5398 (19)C10—H10C0.9800
C4—H41.0000C11—H11A0.9900
C5—C101.524 (2)C11—H11B0.9900
C5—C61.555 (2)
C1—O1—H1111.6 (16)C11—C6—C5115.48 (13)
C4—O2—H2107.9 (17)C7—C6—H6107.8
C11—O3—H3111.0 (16)C11—C6—H6107.8
O1—C1—C2112.06 (14)C5—C6—H6107.8
O1—C1—H1A109.2C8—C7—C6124.90 (16)
C2—C1—H1A109.2C8—C7—H7117.6
O1—C1—H1B109.2C6—C7—H7117.6
C2—C1—H1B109.2C7—C8—H8A120.0
H1A—C1—H1B107.9C7—C8—H8B120.0
C3—C2—C1127.14 (15)H8A—C8—H8B120.0
C3—C2—H2A116.4C3—C9—H9A109.5
C1—C2—H2A116.4C3—C9—H9B109.5
C2—C3—C9124.29 (15)H9A—C9—H9B109.5
C2—C3—C4118.91 (14)C3—C9—H9C109.5
C9—C3—C4116.71 (13)H9A—C9—H9C109.5
O2—C4—C3110.20 (11)H9B—C9—H9C109.5
O2—C4—C5106.17 (11)C5—C10—H10A109.5
C3—C4—C5114.31 (12)C5—C10—H10B109.5
O2—C4—H4108.7H10A—C10—H10B109.5
C3—C4—H4108.7C5—C10—H10C109.5
C5—C4—H4108.7H10A—C10—H10C109.5
C10—C5—C4111.40 (12)H10B—C10—H10C109.5
C10—C5—C6113.05 (12)O3—C11—C6111.09 (12)
C4—C5—C6112.07 (11)O3—C11—H11A109.4
C10—C5—H5106.6C6—C11—H11A109.4
C4—C5—H5106.6O3—C11—H11B109.4
C6—C5—H5106.6C6—C11—H11B109.4
C7—C6—C11107.85 (12)H11A—C11—H11B108.0
C7—C6—C5109.84 (13)
O1—C1—C2—C3145.42 (16)C3—C4—C5—C6177.87 (12)
C1—C2—C3—C90.9 (2)C10—C5—C6—C773.56 (16)
C1—C2—C3—C4177.31 (14)C4—C5—C6—C7159.53 (12)
C2—C3—C4—O2116.83 (15)C10—C5—C6—C1148.64 (17)
C9—C3—C4—O259.86 (16)C4—C5—C6—C1178.26 (15)
C2—C3—C4—C5123.71 (15)C11—C6—C7—C8117.18 (19)
C9—C3—C4—C559.60 (17)C5—C6—C7—C8116.18 (19)
O2—C4—C5—C10171.78 (13)C7—C6—C11—O3173.22 (14)
C3—C4—C5—C1050.08 (17)C5—C6—C11—O363.52 (17)
O2—C4—C5—C660.43 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.91 (2)1.77 (2)2.6681 (16)166 (3)
O3—H3···O2ii0.89 (2)1.83 (2)2.6983 (16)166 (2)
O1—H1···O3iii0.92 (2)1.83 (2)2.7458 (17)172 (2)
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y, z; (iii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.914 (19)1.77 (2)2.6681 (16)166 (3)
O3—H3···O2ii0.89 (2)1.83 (2)2.6983 (16)166 (2)
O1—H1···O3iii0.922 (19)1.830 (19)2.7458 (17)172 (2)
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y, z; (iii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC11H20O3
Mr200.27
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)5.8932 (9), 7.1714 (9), 27.347 (4)
V3)1155.7 (3)
Z4
Radiation typeCu Kα
µ (mm1)0.66
Crystal size (mm)0.22 × 0.10 × 0.05
Data collection
DiffractometerBruker D8 VENTURE CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2012)
No. of measured, independent and
observed [I > 2σ(I)] reflections
7921, 2189, 2154
Rint0.025
(sin θ/λ)max1)0.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.080, 1.10
No. of reflections2189
No. of parameters141
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.17
Absolute structureFlack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Absolute structure parameter0.06 (4)

Computer programs: SMART (Bruker, 2012), SAINT (Bruker, 2012), SHELXD (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

 

Acknowledgements

Financial support by the Fonds der Chemischen Industrie (FCI) and the TU Dortmund is gratefully acknowledged.

References

First citationBruker (2012). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChe, Y., Gloer, J. B. & Wicklow, D. T. (2004). Org. Lett. 6, 1249–1252.  CrossRef PubMed CAS Google Scholar
First citationEvans, D. A., Miller, S. J., Lectka, T. & von Matt, P. (1999). J. Am. Chem. Soc. 121, 7559–7573.  Web of Science CrossRef CAS Google Scholar
First citationJaschinski, T. & Hiersemann, M. (2012). Org. Lett. 14, 4114–4117.  CrossRef CAS PubMed Google Scholar
First citationKörner, M. & Hiersemann, M. (2007). Org. Lett. 9, 4979–4982.  Web of Science PubMed Google Scholar
First citationLiu, H., Yip, J. & Shia, K. S. (1997). Tetrahedron Lett. 38, 2253–2256.  CrossRef CAS Google Scholar
First citationParsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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