(2SR,3SR)-Isopropyl 3-{[dimeth­yl(phenyl)­sil­yl]meth­yl}-2-hy­droxy-2-vinyl­pent-4-enoate

Nelson, B.; Schürmann, M.; Preut, H.; Hiersemann, M.

doi:10.1107/S1600536810044818

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3102

https://doi.org/10.1107/S1600536810044818

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(2SR,3SR)-Isopropyl 3-{[dimethyl(phenyl)silyl]methyl}-2-hydroxy-2-vinylpent-4-enoate

Bjoern Nelson,^a Markus Schürmann,^a Hans Preut ^a ^* and Martin Hiersemann ^a

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

(Received 30 September 2010; accepted 2 November 2010; online 6 November 2010)

The relative configuration of the title compound, C₁₉H₂₈O₃Si, which was synthesized using a dienolate-[2,3]-Wittig rearrangement, was corroborated by single-crystal X-ray diffraction analysis. The Si—C bond distances are in the range 1.858 (2)–1.880 (2) Å and an intramolecular O—H⋯O hydrogen bond helps to stabilize the molecular conformation.

Related literature

For background literature on Wittig rearrangements, see: Abraham et al. (2003 ); Hiersemann (1999 , 2000 ); Lauterbach et al. (1999 ); Le Menez et al. (1995 ).

Experimental

Crystal data

C₁₉H₂₈O₃Si
M_r = 332.50
Monoclinic, C c
a = 18.4311 (15) Å
b = 12.0676 (10) Å
c = 8.8508 (6) Å
β = 95.366 (7)°
V = 1960.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 173 K
0.44 × 0.12 × 0.10 mm

Data collection

Oxford Xcalibur S CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.92, T_max = 1.00
6497 measured reflections
3425 independent reflections
2466 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.044
S = 1.01
3425 reflections
213 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1066 Friedel pairs
Flack parameter: 0.09 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.84	2.17	2.664 (2)	118

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis CCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810044818/hb5668sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044818/hb5668Isup2.hkl

checkCIF report

Comment top

The title compound I was synthesized from allylic alcohol (Le Menez et al., 1995), followed by diastereoselective dienolate-[2,3]-Wittig rearrangement (Lauterbach et al., 1999). Fig. 1 depicts the structure of isolated racemic major diastereomer of I. The relative configuration of the stereogenic centers in I can be attributed to the stereochemical course of the dienolate-[2,3]-Wittig rearrangement (Hiersemann, 1999, 2000; Abraham et al., 2003).

Related literature top

For background literature on Wittig rearrangements, see: Abraham et al. (2003); Hiersemann (1999, 2000); Lauterbach et al. (1999); Le Menez et al. (1995).

Experimental top

To a cooled (195 K) solution of LDA [prepared in situ from NEt₃ (4.2 mmol, 0.6 ml, 1.4 eq) and n-BuLi (2.3 M in hexanes, 4.2 mmol, 1.8 ml, 1.4 eq) in THF (15 ml, 3.5 ml/mmol NEt₃) was added dropwise a pre-cooled (195 K) solution of the allyl vinyl ether II ((Z,E)/(E,E) = 3/2, 3.0 mmol, 1 g, 1 eq) in THF (6 ml, 2 ml/mmol II). The reaction mixture was stirred at 195 K for 30 min, warmed to 273 K and stirred for an additional 60 min. After the addition of saturated aqueous NH₄Cl solution the aqueous layer was extracted with CH₂Cl₂ (3×) and the combined organic phases were dried (MgSO₄) and concentrated under reduced pressure. Purification by flash chromatography (cyclohexane/ethyl acetate 100/1 to 50/1) afforded the 1,5-hexadiene I (813 mg, 2.44 mmol, 82%) as a mixture of diastereomers (dr = 86/14) as colourless crystals. Subsequent recrystallization of I by vapour diffusion technique from isohexane and ethyl acetate provided colourless needles of the major diastereomer of (I) suitable for an X-ray crystal structure analysis.

R_f 0.60 (cyclohexane/ethyl acetate 5/1); ¹H NMR (CDCl₃, 400 MHZ, δ): 0.23 (s, 3H^minor, CH₃), 0.24 (s, 3H^major, CH₃), 0.26 (s, 3H^minor, CH₃), 0.27 (s, 3H^major, CH₃), 0.58 (dd, J = 14.6, 2.0 Hz, 2H^major, CH₂), 0.86 (dd, J = 15.1, 12.1 Hz, 2H^{minor, CH}₂), 1.03 (dd, J = 14.8, 2.3 Hz, 2H^minor, CH₂), 1.10 (dd, J = 14.6, 12.6 Hz, 2H^major, CH₂), 1.20–1.24 (m, 6H, 2 × CH₃), 2.50 (ddd, J = 12.1, 9.8, 2.3 Hz, 1H^minor, CH), 2.59 (ddd, J = 12.6, 9.8, 2.0 Hz, 1H^major, CH), 3.29 (s, 1H^minor, OH), 3.33 (s, 1H^major, OH), 4.88–5.07 (m, 3 × 1H, CH), 5.13 (dd, J = 10.5, 1,5 Hz, 1H^major, H₂C═), 5.23 (dd, J = 10.5, 1,5 Hz, 1H^minor, H₂C═), 5.37 (dd, J = 17.1, 1,5 Hz, 1H^major, H₂C═), 5.42–5.52 (m, 1H^major+1H^minor, CH), 5.56–5.65 (m, 1H^minor, CH), 5.78 (dd, J = 16.8, 10,3 Hz, 1H^minor, H₂C═), 5.81 (dd, J = 17.1, 10.5 Hz, 1H^major, H₂C═), 7.31–7.35 (m, 3H, 3 × CH^Ar), 7.42–7.48 (m, 2H, 2 × CH^Ar); ¹³C NMR (CDCl₃, 101 MHz, δ): -2.4 (CH₃^minor), -2.3 (CH₃^major), -1.5 (CH₃^minor), -1.4 (CH₃^major), 13.8 (CH₂^minor), 15.8 (CH₂^{major), 21.8 (CH}₃), 21.8 (CH₃^minor), 21.9 (CH₂^major),47.6 (CH^minor), 47.8 (CH^major), 70.3 (CH), 80.9 (C^major), 81.0 (C^minor), 115.3 (CH₂^major), 116.6 (CH₂^minor), 117.4 (CH₂^minor), 117.8 (CH₂^major), 127.7 (CH^minor), 127.8 (CH^major), 128.9 (CH^minor), 129.0 (CH^major), 133.7 (CH^major), 133.8 (CH^minor), 138.0 (CH^minor), 138.0 (CH^major), 138.3 (CH^major), 138.8 (CH^minor), 139.4 (C), 174.6 (C); IR (cm^-1): 3505 (br,s) (ν OH), 3070 (w), 3050 (w), 3020 (w), 2980 (m), 2955 (m), 2920 (w), 1725 (s) (ν C═O), 1640 (w), 1620 (w), 1470 (w), 1455 (w), 1430 (m), 1400 (w), 1390 (w), 1375 (m), 1260 (s), 1190 (s), 1140 (m), 1105 (s), 1085 (m); Anal. Calcd. for C₁₉H₂₈O₃Si: C, 68.6; H, 8.5; Found: C, 68.6; H,8.2; M = 332.51 g/mol.

Structure description top

For background literature on Wittig rearrangements, see: Abraham et al. (2003); Hiersemann (1999, 2000); Lauterbach et al. (1999); Le Menez et al. (1995).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids shown at the 30% probability level.

(2SR,3SR)-Isopropyl 3-{[dimethyl(phenyl)silyl]methyl}-2-hydroxy-2-vinylpent-4-enoate top

Crystal data top

C₁₉H₂₈O₃Si	F(000) = 720
M_r = 332.50	D_x = 1.127 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2622 reflections
a = 18.4311 (15) Å	θ = 2.2–29.1°
b = 12.0676 (10) Å	µ = 0.13 mm⁻¹
c = 8.8508 (6) Å	T = 173 K
β = 95.366 (7)°	Block, colourless
V = 1960.0 (3) Å³	0.44 × 0.12 × 0.10 mm
Z = 4

Data collection top

Oxford Xcalibur S CCD diffractometer	3425 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2466 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 16.0560 pixels mm^-1	θ_max = 25.5°, θ_min = 2.2°
ω scans	h = −21→22
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −14→14
T_min = 0.92, T_max = 1.00	l = −10→10
6497 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.044	w = 1/[σ²(F_o²)
S = 1.01	(Δ/σ)_max = 0.001
3425 reflections	Δρ_max = 0.28 e Å⁻³
213 parameters	Δρ_min = −0.21 e Å⁻³
2 restraints	Absolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (9)

Crystal data top

C₁₉H₂₈O₃Si	V = 1960.0 (3) Å³
M_r = 332.50	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 18.4311 (15) Å	µ = 0.13 mm⁻¹
b = 12.0676 (10) Å	T = 173 K
c = 8.8508 (6) Å	0.44 × 0.12 × 0.10 mm
β = 95.366 (7)°

Data collection top

Oxford Xcalibur S CCD diffractometer	3425 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	2466 reflections with I > 2σ(I)
T_min = 0.92, T_max = 1.00	R_int = 0.035
6497 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.044	Δρ_max = 0.28 e Å⁻³
S = 1.01	Δρ_min = −0.21 e Å⁻³
3425 reflections	Absolute structure: Flack (1983), with how many Friedel pairs?
213 parameters	Absolute structure parameter: 0.09 (9)
2 restraints

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	U_iso*/U_eq
Si	0.22320 (4)	0.22241 (6)	0.31540 (6)	0.02606 (19)
C1	0.17453 (12)	0.2779 (2)	0.4769 (2)	0.0203 (6)
O1	0.42490 (8)	0.24617 (13)	0.68996 (16)	0.0266 (5)
O2	0.50238 (10)	0.17136 (15)	0.53585 (17)	0.0373 (5)
C2	0.17399 (13)	0.2176 (2)	0.6094 (2)	0.0271 (7)
H2	0.1974	0.1474	0.6173	0.033*
O3	0.46978 (10)	0.32269 (15)	0.32107 (15)	0.0304 (5)
H3	0.4988	0.2689	0.3297	0.046*
C3	0.13979 (16)	0.2578 (2)	0.7307 (3)	0.0375 (8)
H3A	0.1404	0.2155	0.8213	0.045*
C4	0.10492 (15)	0.3585 (2)	0.7211 (3)	0.0343 (8)
H4	0.0810	0.3856	0.8042	0.041*
C5	0.10492 (16)	0.4195 (2)	0.5904 (3)	0.0353 (7)
H5	0.0811	0.4894	0.5828	0.042*
C6	0.13942 (14)	0.3794 (2)	0.4699 (2)	0.0263 (7)
H6	0.1391	0.4225	0.3800	0.032*
C7	0.32344 (12)	0.2331 (2)	0.3641 (2)	0.0251 (6)
H7A	0.3377	0.1759	0.4413	0.030*
H7B	0.3475	0.2140	0.2722	0.030*
C8	0.35493 (12)	0.3452 (2)	0.4244 (2)	0.0200 (6)
H8	0.3331	0.3620	0.5211	0.024*
C9	0.43837 (13)	0.3388 (2)	0.4608 (2)	0.0224 (6)
C10	0.45930 (13)	0.2409 (2)	0.5653 (3)	0.0213 (7)
C11	0.44411 (16)	0.1640 (2)	0.8072 (3)	0.0338 (8)
H11	0.4981	0.1532	0.8184	0.041*
C12	0.40720 (19)	0.0556 (2)	0.7641 (3)	0.0637 (11)
H12A	0.4224	0.0303	0.6667	0.096*
H12B	0.3542	0.0659	0.7553	0.096*
H12C	0.4210	0.0001	0.8425	0.096*
C13	0.20207 (15)	0.0718 (2)	0.2902 (3)	0.0478 (9)
H13A	0.2285	0.0419	0.2082	0.072*
H13B	0.1496	0.0621	0.2645	0.072*
H13C	0.2170	0.0322	0.3847	0.072*
C14	0.19202 (14)	0.2949 (2)	0.1357 (2)	0.0411 (8)
H14A	0.1999	0.3748	0.1485	0.062*
H14B	0.1400	0.2805	0.1098	0.062*
H14C	0.2197	0.2677	0.0540	0.062*
C15	0.33501 (13)	0.4375 (2)	0.3156 (2)	0.0225 (7)
H15	0.3503	0.4310	0.2164	0.027*
C16	0.29856 (14)	0.5262 (2)	0.3452 (3)	0.0367 (8)
H16A	0.2823	0.5361	0.4430	0.044*
H16B	0.2883	0.5809	0.2690	0.044*
C17	0.46867 (14)	0.4419 (2)	0.5398 (3)	0.0278 (7)
H17	0.4481	0.4647	0.6292	0.033*
C18	0.52116 (15)	0.5018 (2)	0.4934 (3)	0.0445 (8)
H18A	0.5429	0.4813	0.4044	0.053*
H18B	0.5376	0.5659	0.5488	0.053*
C19	0.42038 (18)	0.2118 (2)	0.9503 (3)	0.0549 (10)
H19A	0.4444	0.2834	0.9707	0.082*
H19B	0.4338	0.1610	1.0348	0.082*
H19C	0.3674	0.2221	0.9394	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si	0.0214 (5)	0.0303 (5)	0.0268 (4)	−0.0022 (5)	0.0040 (3)	−0.0070 (4)
C1	0.0163 (16)	0.0245 (16)	0.0198 (14)	−0.0033 (15)	−0.0006 (12)	0.0011 (14)
O1	0.0297 (12)	0.0260 (12)	0.0247 (9)	0.0058 (9)	0.0058 (8)	0.0037 (8)
O2	0.0312 (14)	0.0389 (14)	0.0432 (12)	0.0143 (11)	0.0103 (10)	0.0044 (10)
C2	0.0278 (18)	0.0244 (16)	0.0290 (14)	0.0001 (15)	0.0017 (13)	0.0041 (14)
O3	0.0249 (13)	0.0384 (14)	0.0300 (10)	0.0074 (10)	0.0143 (9)	0.0014 (9)
C3	0.047 (2)	0.044 (2)	0.0217 (14)	−0.0211 (17)	0.0032 (13)	0.0031 (14)
C4	0.033 (2)	0.039 (2)	0.0348 (17)	−0.0160 (16)	0.0202 (14)	−0.0153 (15)
C5	0.0300 (19)	0.0297 (19)	0.0481 (16)	0.0024 (15)	0.0126 (14)	−0.0056 (16)
C6	0.0240 (18)	0.0287 (18)	0.0261 (14)	0.0005 (14)	0.0029 (13)	0.0064 (13)
C7	0.0236 (16)	0.0261 (17)	0.0256 (13)	−0.0003 (14)	0.0025 (11)	−0.0014 (13)
C8	0.0201 (18)	0.0242 (17)	0.0164 (11)	0.0007 (13)	0.0050 (11)	−0.0020 (12)
C9	0.0176 (18)	0.0270 (18)	0.0234 (14)	0.0007 (13)	0.0065 (12)	0.0019 (13)
C10	0.0158 (19)	0.0235 (19)	0.0239 (14)	−0.0067 (14)	−0.0018 (13)	−0.0014 (13)
C11	0.032 (2)	0.038 (2)	0.0309 (16)	0.0057 (16)	−0.0018 (14)	0.0100 (15)
C12	0.104 (3)	0.035 (2)	0.0538 (19)	−0.021 (2)	0.014 (2)	0.0047 (17)
C13	0.039 (2)	0.044 (2)	0.0622 (19)	−0.0111 (16)	0.0144 (16)	−0.0227 (17)
C14	0.0227 (18)	0.073 (2)	0.0273 (14)	−0.0045 (17)	−0.0008 (13)	−0.0037 (15)
C15	0.0206 (17)	0.0261 (18)	0.0211 (13)	−0.0022 (14)	0.0044 (12)	0.0028 (13)
C16	0.039 (2)	0.034 (2)	0.0363 (16)	0.0047 (16)	0.0031 (15)	0.0064 (14)
C17	0.0202 (18)	0.029 (2)	0.0336 (15)	−0.0023 (14)	0.0000 (13)	−0.0064 (14)
C18	0.040 (2)	0.037 (2)	0.0553 (19)	−0.0103 (18)	−0.0019 (16)	−0.0032 (16)
C19	0.092 (3)	0.046 (2)	0.0287 (16)	0.004 (2)	0.0137 (17)	0.0057 (16)

Geometric parameters (Å, º) top

Si—C14	1.859 (2)	C9—C17	1.508 (3)
Si—C7	1.862 (2)	C9—C10	1.527 (3)
Si—C13	1.868 (2)	C11—C19	1.494 (3)
Si—C1	1.880 (2)	C11—C12	1.507 (3)
C1—C2	1.381 (3)	C11—H11	1.0000
C1—C6	1.385 (3)	C12—H12A	0.9800
O1—C10	1.325 (2)	C12—H12B	0.9800
O1—C11	1.454 (3)	C12—H12C	0.9800
O2—C10	1.200 (3)	C13—H13A	0.9800
C2—C3	1.383 (3)	C13—H13B	0.9800
C2—H2	0.9500	C13—H13C	0.9800
O3—C9	1.427 (2)	C14—H14A	0.9800
O3—H3	0.8400	C14—H14B	0.9800
C3—C4	1.373 (3)	C14—H14C	0.9800
C3—H3A	0.9500	C15—C16	1.303 (3)
C4—C5	1.371 (3)	C15—H15	0.9500
C4—H4	0.9500	C16—H16A	0.9500
C5—C6	1.379 (3)	C16—H16B	0.9500
C5—H5	0.9500	C17—C18	1.304 (3)
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.547 (3)	C18—H18A	0.9500
C7—H7A	0.9900	C18—H18B	0.9500
C7—H7B	0.9900	C19—H19A	0.9800
C8—C15	1.496 (3)	C19—H19B	0.9800
C8—C9	1.543 (3)	C19—H19C	0.9800
C8—H8	1.0000

C14—Si—C7	112.71 (11)	O2—C10—C9	123.0 (2)
C14—Si—C13	108.16 (12)	O1—C10—C9	110.7 (2)
C7—Si—C13	106.64 (12)	O1—C11—C19	105.7 (2)
C14—Si—C1	110.59 (11)	O1—C11—C12	109.7 (2)
C7—Si—C1	109.45 (10)	C19—C11—C12	112.8 (2)
C13—Si—C1	109.15 (12)	O1—C11—H11	109.5
C2—C1—C6	117.6 (2)	C19—C11—H11	109.5
C2—C1—Si	119.99 (19)	C12—C11—H11	109.5
C6—C1—Si	122.36 (17)	C11—C12—H12A	109.5
C10—O1—C11	117.3 (2)	C11—C12—H12B	109.5
C3—C2—C1	121.0 (2)	H12A—C12—H12B	109.5
C3—C2—H2	119.5	C11—C12—H12C	109.5
C1—C2—H2	119.5	H12A—C12—H12C	109.5
C9—O3—H3	109.5	H12B—C12—H12C	109.5
C4—C3—C2	120.5 (2)	Si—C13—H13A	109.5
C4—C3—H3A	119.8	Si—C13—H13B	109.5
C2—C3—H3A	119.8	H13A—C13—H13B	109.5
C5—C4—C3	119.3 (2)	Si—C13—H13C	109.5
C5—C4—H4	120.3	H13A—C13—H13C	109.5
C3—C4—H4	120.3	H13B—C13—H13C	109.5
C4—C5—C6	120.1 (2)	Si—C14—H14A	109.5
C4—C5—H5	120.0	Si—C14—H14B	109.5
C6—C5—H5	120.0	H14A—C14—H14B	109.5
C1—C6—C5	121.5 (2)	Si—C14—H14C	109.5
C1—C6—H6	119.2	H14A—C14—H14C	109.5
C5—C6—H6	119.2	H14B—C14—H14C	109.5
C8—C7—Si	118.22 (17)	C16—C15—C8	125.6 (2)
C8—C7—H7A	107.8	C16—C15—H15	117.2
Si—C7—H7A	107.8	C8—C15—H15	117.2
C8—C7—H7B	107.8	C15—C16—H16A	120.0
Si—C7—H7B	107.8	C15—C16—H16B	120.0
H7A—C7—H7B	107.1	H16A—C16—H16B	120.0
C15—C8—C9	110.6 (2)	C18—C17—C9	124.4 (2)
C15—C8—C7	111.55 (18)	C18—C17—H17	117.8
C9—C8—C7	111.3 (2)	C9—C17—H17	117.8
C15—C8—H8	107.8	C17—C18—H18A	120.0
C9—C8—H8	107.8	C17—C18—H18B	120.0
C7—C8—H8	107.8	H18A—C18—H18B	120.0
O3—C9—C17	110.6 (2)	C11—C19—H19A	109.5
O3—C9—C10	108.6 (2)	C11—C19—H19B	109.5
C17—C9—C10	107.24 (19)	H19A—C19—H19B	109.5
O3—C9—C8	107.62 (18)	C11—C19—H19C	109.5
C17—C9—C8	112.0 (2)	H19A—C19—H19C	109.5
C10—C9—C8	110.8 (2)	H19B—C19—H19C	109.5
O2—C10—O1	126.3 (3)

C14—Si—C1—C2	162.39 (19)	C7—C8—C9—O3	66.2 (2)
C7—Si—C1—C2	−72.9 (2)	C15—C8—C9—C17	63.3 (2)
C13—Si—C1—C2	43.5 (2)	C7—C8—C9—C17	−172.12 (17)
C14—Si—C1—C6	−18.7 (2)	C15—C8—C9—C10	−177.0 (2)
C7—Si—C1—C6	106.0 (2)	C7—C8—C9—C10	−52.4 (2)
C13—Si—C1—C6	−137.6 (2)	C11—O1—C10—O2	4.0 (4)
C6—C1—C2—C3	−0.3 (3)	C11—O1—C10—C9	−174.6 (2)
Si—C1—C2—C3	178.7 (2)	O3—C9—C10—O2	8.1 (3)
C1—C2—C3—C4	0.7 (4)	C17—C9—C10—O2	−111.4 (3)
C2—C3—C4—C5	−0.7 (4)	C8—C9—C10—O2	126.1 (3)
C3—C4—C5—C6	0.3 (4)	O3—C9—C10—O1	−173.21 (19)
C2—C1—C6—C5	−0.1 (4)	C17—C9—C10—O1	67.3 (2)
Si—C1—C6—C5	−179.0 (2)	C8—C9—C10—O1	−55.2 (3)
C4—C5—C6—C1	0.1 (4)	C10—O1—C11—C19	159.6 (2)
C14—Si—C7—C8	74.11 (18)	C10—O1—C11—C12	−78.5 (3)
C13—Si—C7—C8	−167.35 (17)	C9—C8—C15—C16	−114.6 (3)
C1—Si—C7—C8	−49.40 (18)	C7—C8—C15—C16	121.0 (3)
Si—C7—C8—C15	−56.7 (2)	O3—C9—C17—C18	−6.0 (4)
Si—C7—C8—C9	179.26 (14)	C10—C9—C17—C18	112.3 (3)
C15—C8—C9—O3	−58.4 (3)	C8—C9—C17—C18	−126.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84	2.17	2.664 (2)	118

Experimental details

Crystal data
Chemical formula	C₁₉H₂₈O₃Si
M_r	332.50
Crystal system, space group	Monoclinic, Cc
Temperature (K)	173
a, b, c (Å)	18.4311 (15), 12.0676 (10), 8.8508 (6)
β (°)	95.366 (7)
V (Å³)	1960.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.44 × 0.12 × 0.10

Data collection
Diffractometer	Oxford Xcalibur S CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.92, 1.00
No. of measured, independent and observed [I > 2σ(I)] reflections	6497, 3425, 2466
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.044, 1.01
No. of reflections	3425
No. of parameters	213
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21
Absolute structure	Flack (1983), with how many Friedel pairs?
Absolute structure parameter	0.09 (9)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.84	2.17	2.664 (2)	118

References

Abraham, L., Pollex, A. & Hiersemann, M. (2003). Synlett, pp. 1088–1095. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hiersemann, M. (1999). Tetrahedron, 55, 2625–2638. Web of Science CrossRef CAS Google Scholar
Hiersemann, M. (2000). Synthesis, pp. 1279–1290. CrossRef Google Scholar
Lauterbach, C., Pollex, A. & Hiersemann, M. (1999). Eur. J. Org. Chem. pp. 2713–2724. Google Scholar
Le Menez, P., Fargeas, V., Berque, I., Poisson, J. & Ardisson, J. (1995). J. Org. Chem. 60, 3592–3599. CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2SR,3SR)-Iso­propyl 3-{[dimeth­yl(phenyl)­sil­yl]meth­yl}-2-hy­dr­oxy-2-vinyl­pent-4-enoate

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Experimental

Crystal data

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organic compounds

(2SR,3SR)-Isopropyl 3-{[dimethyl(phenyl)silyl]methyl}-2-hydroxy-2-vinylpent-4-enoate