(3R,4S,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]tetra­hydro­furan-2-one

Becker, A.; Schürmann, M.; Preut, H.; Hiersemann, M.

doi:10.1107/S1600536808021181

organic compounds

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Volume 64| Part 8| August 2008| Page o1517

doi:10.1107/S1600536808021181

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(3R,4S,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]tetrahydrofuran-2-one

Annika Becker,^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@udo.edu

(Received 30 May 2008; accepted 8 July 2008; online 16 July 2008)

The title compound, C₁₁H₁₈O₃, was synthesized to prove the relative configuration of the corresponding acyclic C1—C8 stereopentade. It crystallizes with two molecules in the asymmetric unit, which show only slight differences. The molecules are linked via O—H⋯O hydrogen bonds, resulting in two crystallographically independent chains of molecules propagating in the a-axis direction. The absolute configuration was known from the synthesis.

Related literature

For related literature, see: Abraham, Körner & Hiersemann (2004 ); Abraham, Körner, Schwab & Hiersemann (2004 ); Corey & Snider (1972 ); Evans et al. (1981 , 1999 ); Körner & Hiersemann (2006 , 2007 ); Pollex & Hiersemann (2005 ).

Experimental

Crystal data

C₁₁H₁₈O₃
M_r = 198.25
Monoclinic, P 2₁
a = 6.2934 (13) Å
b = 16.411 (3) Å
c = 11.607 (2) Å
β = 95.46 (3)°
V = 1193.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 (1) K
0.30 × 0.28 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
9263 measured reflections
2268 independent reflections
1228 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.080
S = 1.06
2268 reflections
262 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.82	2.03	2.821 (3)	163
O2′—H2′⋯O3′ⁱ	0.82	1.96	2.771 (3)	171
Symmetry code: (i) x+1, y, z.

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, 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, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021181/hb2741sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021181/hb2741Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was synthesized using a catalytic asymmetric Claisen rearrangement (Abraham et al., 2004a; Abraham et al. 2004b; Pollex & Hiersemann, 2005; Körner & Hiersemann, 2006; Körner & Hiersemann, 2007), a diastereoselective reduction with K-Selectride (Körner & Hiersemann, 2006; Körner & Hiersemann, 2007), and an aldol addition under modified Evans conditions (Evans et al., 1981). In order to verify the relative configuration of the major diastereomer of the obtained aldol adduct (dr = 7/3), 4-(tert-butyldimethylsilyloxy)-3-hydroxy-2,5,6-trimethyloct-7-enoyl)-4-isopropyloxazolidin-2-one, (II), a γ-lactone, (I), was prepared by removal of the silyl protecting group (Corey et al., 1972) and subsequent in situ lactonization. Fig. 1 depicts the structure of the isolated major diastereomer (I). The configuration of the chiral C atoms in (I) can be attributed to the stereochemical course of the aldol addition (C3 R and C4 S), the diastereoselective reduction with K-Selectride (C5 S), and the catalytic asymmetric Claisen rearrangement (C2 S and C3 R) using the chiral Lewis acid [Cu{(S,S)-tert-Butyl-box}](H₂O)₂(SbF₆)₂ (Evans et al., 1999).

There are two molecules of (I) in the asymmetric unit (Figs. 1 and 2) with similar conformations. In the crystal, the molecules interact via O—H···O hydrogen bonds (Table 1) to form two independent chains, both propagating in [100].

Related literature top

For related literature, see: Abraham, Körner & Hiersemann (2004); Abraham, Körner, Schwab & Hiersemann (2004); Corey & Snider (1972); Evans et al. (1981, 1999); Körner & Hiersemann (2006, 2007); Pollex & Hiersemann (2005).

Experimental top

The title compound, (I), was synthesized from the corresponding anti-aldol adduct, (II), using tetrabutylammonium fluoride (TBAF) (Corey et al., 1972) for the removal of the silyl protecting group. The subsequent lactonization proceeded in situ.

TBAF (1 M in tetrahydrofuran, 0.82 ml, 3.0 eq) was added to a solution of the diastereomeric mixture of (II) (dr = 7/3, 120 mg, 0.27 mmol, 1.0 eq) in dry tetrahydrofuran (2 ml) at 273 K. The mixture was stirred at 273 K for 15 min and then at 298 K for 30 min. The reaction was quenched by the addition of saturated aqueous NaHCO₃ solution. The phases were separated, and the aqueous phase was extracted with CH₂Cl₂. The combined organic layers were dried over MgSO₄ and concentrated under reduced pressure. Flash chromatography (isohexane/ethyl acetate 20/1 to 10/1) afforded (I) as a single diastereomer and additionally a mixture of (I) and the minor diastereomer with an overall yield of 72% (38.7 mg, 0.195 mmol) as colourless crystals. Single crystals of (I) were obtained by vapor diffusion recrystallization technique from isohexane and ethyl acetate to yield colourless cuboids: mp 412 K; R_f 0.33 (cyclohexane/ethyl acetate 2/1); ¹H NMR (CDCl₃, 400 MHz, δ): 0.84 (d, J = 7.0 Hz, 3H, (1)-H), 0.97 (d, J = 7.0 Hz, 3H, (3)'-H), 1.27 (d, J = 7.3 Hz, 3H, 3'-H), 1.85 (d, J = 4.8 Hz, 1H, –OH) overlapped by 1.89 (br. s), 2.19 (dqd, J = 10.6, 7.0, 3.0 Hz, 1H, (2)-H), 2.73 (dq, J = 4.8, 7.3 Hz, 1H, 3-H) overlapped by 2.62 - 2.72 (m, 1H, (3)-H), 4.07 (dd, J = 10.6, 3.0 Hz, 1H, 5-H), 4.37 (dd, J = 7.3, 4.8 Hz, 1H, 4-H), 5.03 (dd, ³J(E) = 17.0 Hz, ²J = 1.3 Hz, 1H, (5)-H), 5.04 (dd, ³J(Z) = 11.0 Hz, ²J = 1.3 Hz, 1H, (5)-H), 5.84 (ddd, ³J(E) = 17.0 Hz, ³J(Z) = 11.0 Hz, ³J = 6.3 Hz, 1H, (4)-H); ¹³C NMR (CDCl₃, 100 MHz, δ): 8.4 (CH₃), 9.7 (CH₃), 12.3 (CH₃), 35.7 (CH), 36.9 (CH), 42.7 (CH), 71.7 (CH), 84.3 (CH), 114.3 (CH₂), 142.7 (CH), 178.4 (C); IR (cm^-1): 3435(br, nm) (ν O—H, OH in H-bridges), 3085(w) 3020(w) (ν C—H, olefin), 2970(m) 2925(m) 2855(s) (ν_as,s C—H, CH₂, CH₃, CH), 1740(s) (ν C=O, lactone), 1640(w) (ν C=C), 1465(m) (δ_as C—H, CH₃, CH₂), 1380(m) (δ_s C—H, CH₃); Anal. Calcd. for C₁₁H₁₈O₃: C, 66.6; H, 9.2; Found: C, 66.5; H, 9.3; [α]_D²⁰ +2.2 (c 0.472, CHCl₃).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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, 2003).

Figures top

	Fig. 1. : The molecular structure of molecule one of (I), with displacement ellipsoids for the non-hydrogen atoms shown at the 30% probability level.
	Fig. 2. : The molecular structure of molecule two of (I), with displacement ellipsoids for the non-hydrogen atoms shown at the 30% probability level.

(3R,4S,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)- 3-methylpent-4-en-2-yl]tetrahydrofuran-2-one top

Crystal data top

C₁₁H₁₈O₃	F(000) = 432
M_r = 198.25	D_x = 1.103 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9263 reflections
a = 6.2934 (13) Å	θ = 3.0–25.4°
b = 16.411 (3) Å	µ = 0.08 mm⁻¹
c = 11.607 (2) Å	T = 291 K
β = 95.46 (3)°	Block, colourless
V = 1193.4 (4) Å³	0.30 × 0.28 × 0.20 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	1228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 25.4°, θ_min = 3.0°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −7→7
259 frames via ω–rotation (Δω=1%) and two times 120 s per frame (three sets at different κ–angles) scans	k = −19→19
9263 measured reflections	l = −13→13
2268 independent 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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0276P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2268 reflections	Δρ_max = 0.14 e Å⁻³
262 parameters	Δρ_min = −0.10 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (4)

Crystal data top

C₁₁H₁₈O₃	V = 1193.4 (4) Å³
M_r = 198.25	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 6.2934 (13) Å	µ = 0.08 mm⁻¹
b = 16.411 (3) Å	T = 291 K
c = 11.607 (2) Å	0.30 × 0.28 × 0.20 mm
β = 95.46 (3)°

Data collection top

Nonius KappaCCD diffractometer	1228 reflections with I > 2σ(I)
9263 measured reflections	R_int = 0.026
2268 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	Δρ_max = 0.14 e Å⁻³
2268 reflections	Δρ_min = −0.10 e Å⁻³
262 parameters

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
O1	−0.2547 (2)	0.96841 (13)	0.63254 (16)	0.0723 (6)
O2	0.1616 (3)	0.91394 (14)	0.55403 (19)	0.0818 (7)
H2	0.2747	0.9160	0.5245	0.123*
O3	−0.4523 (3)	0.95694 (15)	0.46477 (16)	0.0804 (6)
C1	0.0831 (4)	0.99366 (19)	0.5670 (2)	0.0699 (9)
H1	0.1979	1.0342	0.5700	0.084*
C2	−0.0400 (4)	0.9980 (2)	0.6745 (2)	0.0717 (9)
H2A	−0.0512	1.0552	0.6971	0.086*
C3	−0.2854 (5)	0.9770 (2)	0.5177 (3)	0.0677 (8)
C4	−0.0916 (4)	1.0127 (2)	0.4718 (2)	0.0713 (9)
H4	−0.1101	1.0720	0.4700	0.086*
C5	−0.0562 (5)	0.9858 (2)	0.3503 (2)	0.0963 (11)
H5A	−0.0272	0.9284	0.3501	0.144*
H5B	0.0629	1.0149	0.3246	0.144*
H5C	−0.1818	0.9971	0.2992	0.144*
C6	0.0466 (4)	0.9499 (2)	0.7790 (2)	0.0766 (9)
H6	0.0636	0.8934	0.7541	0.092*
C7	0.2689 (5)	0.9825 (2)	0.8203 (3)	0.0999 (12)
H7A	0.3668	0.9687	0.7647	0.150*
H7B	0.3165	0.9585	0.8936	0.150*
H7C	0.2628	1.0406	0.8283	0.150*
C8	−0.1058 (5)	0.9493 (3)	0.8754 (3)	0.0969 (12)
H8	−0.2441	0.9299	0.8397	0.116*
C9	−0.1446 (7)	1.0344 (3)	0.9243 (3)	0.1352 (16)
H9A	−0.2459	1.0306	0.9809	0.203*
H9B	−0.1995	1.0698	0.8626	0.203*
H9C	−0.0125	1.0560	0.9598	0.203*
C10	−0.0295 (7)	0.8869 (4)	0.9651 (4)	0.146 (2)
H10	0.0090	0.8378	0.9327	0.175*
C11	−0.0089 (10)	0.8863 (6)	1.0604 (6)	0.278 (5)
H11A	−0.0428	0.9323	1.1017	0.333*
H11B	0.0422	0.8398	1.0995	0.333*
O1'	−0.6701 (3)	0.71545 (13)	0.46394 (18)	0.0769 (6)
O2'	−0.2446 (3)	0.67928 (15)	0.3828 (2)	0.0935 (7)
H2'	−0.1359	0.6868	0.3505	0.140*
O3'	−0.8637 (4)	0.71727 (16)	0.29367 (18)	0.0963 (8)
C1'	−0.3349 (5)	0.7549 (2)	0.4080 (3)	0.0777 (9)
H1'	−0.2255	0.7974	0.4203	0.093*
C2'	−0.4615 (4)	0.7458 (2)	0.5138 (3)	0.0727 (9)
H2'1	−0.4816	0.8000	0.5465	0.087*
C3'	−0.7005 (5)	0.7353 (2)	0.3510 (3)	0.0794 (10)
C4'	−0.5091 (5)	0.7794 (2)	0.3145 (3)	0.0839 (10)
H4'	−0.5347	0.8379	0.3232	0.101*
C5'	−0.4680 (6)	0.7646 (3)	0.1898 (3)	0.1211 (15)
H5'1	−0.3427	0.7940	0.1730	0.182*
H5'2	−0.5883	0.7831	0.1396	0.182*
H5'3	−0.4468	0.7074	0.1779	0.182*
C6'	−0.3719 (4)	0.6903 (2)	0.6094 (3)	0.0726 (9)
H6'	−0.3515	0.6367	0.5749	0.087*
C7'	−0.1534 (5)	0.7211 (2)	0.6567 (3)	0.0986 (12)
H7'1	−0.0566	0.7169	0.5978	0.148*
H7'2	−0.1013	0.6888	0.7224	0.148*
H7'3	−0.1642	0.7770	0.6797	0.148*
C8'	−0.5233 (5)	0.6788 (2)	0.7046 (3)	0.0773 (9)
H8'	−0.6609	0.6623	0.6647	0.093*
C9'	−0.5664 (6)	0.7563 (3)	0.7697 (3)	0.1204 (14)
H9'1	−0.4354	0.7760	0.8091	0.181*
H9'2	−0.6664	0.7450	0.8252	0.181*
H9'3	−0.6248	0.7968	0.7161	0.181*
C10'	−0.4516 (6)	0.6101 (3)	0.7795 (4)	0.1110 (13)
H10'	−0.4328	0.5614	0.7408	0.133*
C11'	−0.4126 (8)	0.6067 (4)	0.8851 (4)	0.183 (3)
H11C	−0.4276	0.6530	0.9300	0.220*
H11D	−0.3679	0.5579	0.9203	0.220*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0470 (10)	0.0854 (17)	0.0864 (13)	−0.0022 (11)	0.0168 (9)	0.0018 (13)
O2	0.0649 (13)	0.0683 (17)	0.1164 (16)	0.0050 (11)	0.0310 (12)	0.0017 (13)
O3	0.0569 (12)	0.0926 (18)	0.0930 (13)	−0.0018 (13)	0.0134 (11)	0.0007 (13)
C1	0.0543 (17)	0.052 (2)	0.106 (2)	−0.0006 (16)	0.0204 (16)	−0.0009 (18)
C2	0.0513 (16)	0.072 (3)	0.094 (2)	−0.0065 (16)	0.0167 (15)	−0.0091 (19)
C3	0.0549 (18)	0.063 (2)	0.088 (2)	0.0086 (17)	0.0190 (16)	0.0012 (19)
C4	0.0609 (18)	0.065 (2)	0.090 (2)	0.0004 (16)	0.0210 (16)	0.0089 (17)
C5	0.083 (2)	0.112 (3)	0.099 (2)	−0.003 (2)	0.0322 (17)	0.004 (2)
C6	0.0509 (16)	0.091 (3)	0.0888 (19)	−0.0027 (17)	0.0115 (15)	−0.007 (2)
C7	0.0603 (18)	0.125 (4)	0.115 (2)	−0.008 (2)	0.0097 (16)	−0.012 (2)
C8	0.0648 (19)	0.140 (4)	0.087 (2)	−0.003 (2)	0.0156 (18)	−0.007 (3)
C9	0.111 (3)	0.173 (5)	0.128 (3)	0.024 (3)	0.047 (3)	−0.021 (3)
C10	0.106 (3)	0.249 (7)	0.086 (3)	0.007 (4)	0.027 (3)	0.030 (4)
C11	0.147 (5)	0.476 (16)	0.222 (7)	0.051 (7)	0.075 (6)	0.165 (9)
O1'	0.0496 (11)	0.0897 (18)	0.0938 (14)	−0.0022 (11)	0.0186 (10)	0.0066 (12)
O2'	0.0718 (14)	0.0719 (18)	0.1435 (19)	0.0044 (13)	0.0446 (13)	0.0045 (15)
O3'	0.0646 (14)	0.125 (2)	0.1002 (15)	−0.0110 (15)	0.0131 (12)	0.0065 (14)
C1'	0.0634 (19)	0.056 (2)	0.117 (2)	−0.0012 (17)	0.0241 (19)	0.003 (2)
C2'	0.0534 (18)	0.060 (2)	0.106 (2)	−0.0041 (16)	0.0122 (16)	−0.003 (2)
C3'	0.060 (2)	0.086 (3)	0.095 (2)	0.0041 (19)	0.0236 (18)	0.006 (2)
C4'	0.073 (2)	0.069 (3)	0.112 (2)	−0.0002 (18)	0.0255 (19)	0.011 (2)
C5'	0.103 (3)	0.153 (4)	0.114 (3)	−0.008 (3)	0.045 (2)	0.016 (3)
C6'	0.0542 (17)	0.064 (2)	0.101 (2)	0.0017 (16)	0.0160 (16)	−0.005 (2)
C7'	0.0560 (18)	0.097 (3)	0.142 (3)	−0.0047 (19)	0.0043 (18)	−0.004 (2)
C8'	0.0616 (18)	0.079 (3)	0.092 (2)	0.0030 (18)	0.0084 (16)	0.002 (2)
C9'	0.107 (3)	0.128 (4)	0.128 (3)	0.021 (3)	0.019 (2)	−0.026 (3)
C10'	0.078 (2)	0.149 (4)	0.108 (3)	0.001 (3)	0.020 (2)	0.015 (3)
C11'	0.134 (4)	0.252 (7)	0.161 (4)	0.028 (4)	−0.001 (4)	0.069 (5)

Geometric parameters (Å, º) top

O1—C3	1.336 (3)	O1'—C3'	1.347 (3)
O1—C2	1.474 (3)	O1'—C2'	1.470 (3)
O2—C1	1.411 (3)	O2'—C1'	1.408 (4)
O2—H2	0.8200	O2'—H2'	0.8200
O3—C3	1.211 (3)	O3'—C3'	1.206 (3)
C1—C4	1.515 (4)	C1'—C4'	1.521 (4)
C1—C2	1.532 (4)	C1'—C2'	1.533 (4)
C1—H1	0.9800	C1'—H1'	0.9800
C2—C6	1.504 (4)	C2'—C6'	1.503 (4)
C2—H2A	0.9800	C2'—H2'1	0.9800
C3—C4	1.496 (4)	C3'—C4'	1.500 (5)
C4—C5	1.515 (4)	C4'—C5'	1.514 (4)
C4—H4	0.9800	C4'—H4'	0.9800
C5—H5A	0.9600	C5'—H5'1	0.9600
C5—H5B	0.9600	C5'—H5'2	0.9600
C5—H5C	0.9600	C5'—H5'3	0.9600
C6—C7	1.531 (4)	C6'—C7'	1.517 (4)
C6—C8	1.542 (4)	C6'—C8'	1.538 (4)
C6—H6	0.9800	C6'—H6'	0.9800
C7—H7A	0.9600	C7'—H7'1	0.9600
C7—H7B	0.9600	C7'—H7'2	0.9600
C7—H7C	0.9600	C7'—H7'3	0.9600
C8—C10	1.506 (7)	C8'—C10'	1.469 (6)
C8—C9	1.536 (6)	C8'—C9'	1.516 (5)
C8—H8	0.9800	C8'—H8'	0.9800
C9—H9A	0.9600	C9'—H9'1	0.9600
C9—H9B	0.9600	C9'—H9'2	0.9600
C9—H9C	0.9600	C9'—H9'3	0.9600
C10—C11	1.102 (6)	C10'—C11'	1.228 (5)
C10—H10	0.9300	C10'—H10'	0.9300
C11—H11A	0.9300	C11'—H11C	0.9300
C11—H11B	0.9300	C11'—H11D	0.9300

C3—O1—C2	109.6 (2)	C3'—O1'—C2'	109.9 (2)
C1—O2—H2	109.5	C1'—O2'—H2'	109.5
O2—C1—C4	110.5 (3)	O2'—C1'—C4'	111.2 (3)
O2—C1—C2	109.8 (2)	O2'—C1'—C2'	109.3 (3)
C4—C1—C2	101.3 (2)	C4'—C1'—C2'	101.7 (2)
O2—C1—H1	111.6	O2'—C1'—H1'	111.4
C4—C1—H1	111.6	C4'—C1'—H1'	111.4
C2—C1—H1	111.6	C2'—C1'—H1'	111.4
O1—C2—C6	110.1 (2)	O1'—C2'—C6'	110.1 (2)
O1—C2—C1	103.6 (2)	O1'—C2'—C1'	103.3 (2)
C6—C2—C1	117.4 (2)	C6'—C2'—C1'	117.6 (2)
O1—C2—H2A	108.5	O1'—C2'—H2'1	108.5
C6—C2—H2A	108.5	C6'—C2'—H2'1	108.5
C1—C2—H2A	108.5	C1'—C2'—H2'1	108.5
O3—C3—O1	120.9 (2)	O3'—C3'—O1'	120.8 (3)
O3—C3—C4	128.5 (3)	O3'—C3'—C4'	128.8 (3)
O1—C3—C4	110.6 (3)	O1'—C3'—C4'	110.4 (3)
C3—C4—C5	114.5 (3)	C3'—C4'—C5'	114.1 (3)
C3—C4—C1	102.7 (2)	C3'—C4'—C1'	102.4 (3)
C5—C4—C1	117.3 (2)	C5'—C4'—C1'	117.5 (3)
C3—C4—H4	107.3	C3'—C4'—H4'	107.4
C5—C4—H4	107.3	C5'—C4'—H4'	107.4
C1—C4—H4	107.3	C1'—C4'—H4'	107.4
C4—C5—H5A	109.5	C4'—C5'—H5'1	109.5
C4—C5—H5B	109.5	C4'—C5'—H5'2	109.5
H5A—C5—H5B	109.5	H5'1—C5'—H5'2	109.5
C4—C5—H5C	109.5	C4'—C5'—H5'3	109.5
H5A—C5—H5C	109.5	H5'1—C5'—H5'3	109.5
H5B—C5—H5C	109.5	H5'2—C5'—H5'3	109.5
C2—C6—C7	108.6 (3)	C2'—C6'—C7'	109.2 (3)
C2—C6—C8	112.7 (3)	C2'—C6'—C8'	113.0 (2)
C7—C6—C8	112.9 (2)	C7'—C6'—C8'	112.5 (3)
C2—C6—H6	107.5	C2'—C6'—H6'	107.3
C7—C6—H6	107.5	C7'—C6'—H6'	107.3
C8—C6—H6	107.5	C8'—C6'—H6'	107.3
C6—C7—H7A	109.5	C6'—C7'—H7'1	109.5
C6—C7—H7B	109.5	C6'—C7'—H7'2	109.5
H7A—C7—H7B	109.5	H7'1—C7'—H7'2	109.5
C6—C7—H7C	109.5	C6'—C7'—H7'3	109.5
H7A—C7—H7C	109.5	H7'1—C7'—H7'3	109.5
H7B—C7—H7C	109.5	H7'2—C7'—H7'3	109.5
C10—C8—C9	114.5 (3)	C10'—C8'—C9'	114.0 (3)
C10—C8—C6	109.1 (3)	C10'—C8'—C6'	110.1 (3)
C9—C8—C6	113.1 (3)	C9'—C8'—C6'	114.1 (3)
C10—C8—H8	106.5	C10'—C8'—H8'	106.0
C9—C8—H8	106.5	C9'—C8'—H8'	106.0
C6—C8—H8	106.5	C6'—C8'—H8'	106.0
C8—C9—H9A	109.5	C8'—C9'—H9'1	109.5
C8—C9—H9B	109.5	C8'—C9'—H9'2	109.5
H9A—C9—H9B	109.5	H9'1—C9'—H9'2	109.5
C8—C9—H9C	109.5	C8'—C9'—H9'3	109.5
H9A—C9—H9C	109.5	H9'1—C9'—H9'3	109.5
H9B—C9—H9C	109.5	H9'2—C9'—H9'3	109.5
C11—C10—C8	134.4 (8)	C11'—C10'—C8'	130.3 (5)
C11—C10—H10	112.8	C11'—C10'—H10'	114.9
C8—C10—H10	112.8	C8'—C10'—H10'	114.9
C10—C11—H11A	120.0	C10'—C11'—H11C	120.0
C10—C11—H11B	120.0	C10'—C11'—H11D	120.0
H11A—C11—H11B	120.0	H11C—C11'—H11D	120.0

C3—O1—C2—C6	−148.1 (3)	C3'—O1'—C2'—C6'	−149.0 (3)
C3—O1—C2—C1	−21.8 (3)	C3'—O1'—C2'—C1'	−22.6 (3)
O2—C1—C2—O1	−83.7 (3)	O2'—C1'—C2'—O1'	−84.1 (3)
C4—C1—C2—O1	33.2 (3)	C4'—C1'—C2'—O1'	33.5 (3)
O2—C1—C2—C6	37.9 (3)	O2'—C1'—C2'—C6'	37.4 (4)
C4—C1—C2—C6	154.7 (3)	C4'—C1'—C2'—C6'	155.1 (3)
C2—O1—C3—O3	−179.6 (3)	C2'—O1'—C3'—O3'	−178.9 (3)
C2—O1—C3—C4	0.5 (3)	C2'—O1'—C3'—C4'	1.6 (3)
O3—C3—C4—C5	−30.6 (5)	O3'—C3'—C4'—C5'	−31.2 (6)
O1—C3—C4—C5	149.3 (3)	O1'—C3'—C4'—C5'	148.3 (3)
O3—C3—C4—C1	−158.8 (3)	O3'—C3'—C4'—C1'	−159.3 (4)
O1—C3—C4—C1	21.1 (3)	O1'—C3'—C4'—C1'	20.2 (4)
O2—C1—C4—C3	84.0 (3)	O2'—C1'—C4'—C3'	84.1 (3)
C2—C1—C4—C3	−32.4 (3)	C2'—C1'—C4'—C3'	−32.2 (3)
O2—C1—C4—C5	−42.5 (4)	O2'—C1'—C4'—C5'	−41.7 (4)
C2—C1—C4—C5	−158.9 (3)	C2'—C1'—C4'—C5'	−158.0 (3)
O1—C2—C6—C7	−179.8 (2)	O1'—C2'—C6'—C7'	178.0 (2)
C1—C2—C6—C7	62.1 (4)	C1'—C2'—C6'—C7'	60.1 (4)
O1—C2—C6—C8	−54.0 (4)	O1'—C2'—C6'—C8'	−56.0 (4)
C1—C2—C6—C8	−172.1 (3)	C1'—C2'—C6'—C8'	−173.9 (3)
C2—C6—C8—C10	168.6 (3)	C2'—C6'—C8'—C10'	166.5 (3)
C7—C6—C8—C10	−67.9 (5)	C7'—C6'—C8'—C10'	−69.3 (4)
C2—C6—C8—C9	−62.7 (4)	C2'—C6'—C8'—C9'	−63.8 (4)
C7—C6—C8—C9	60.8 (4)	C7'—C6'—C8'—C9'	60.4 (4)
C9—C8—C10—C11	7.2 (9)	C9'—C8'—C10'—C11'	−3.6 (7)
C6—C8—C10—C11	135.1 (8)	C6'—C8'—C10'—C11'	126.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	2.03	2.821 (3)	163
O2′—H2′···O3′ⁱ	0.82	1.96	2.771 (3)	171

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₈O₃
M_r	198.25
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	291
a, b, c (Å)	6.2934 (13), 16.411 (3), 11.607 (2)
β (°)	95.46 (3)
V (Å³)	1193.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.28 × 0.20

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9263, 2268, 1228
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.080, 1.06
No. of reflections	2268
No. of parameters	262
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.10

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	2.03	2.821 (3)	163
O2'—H2'···O3'ⁱ	0.82	1.96	2.771 (3)	171

Symmetry code: (i) x+1, y, z.

References

Abraham, L., Körner, M. & Hiersemann, M. (2004). Tetrahedron Lett. 45, 3647–3650. Web of Science CrossRef CAS Google Scholar
Abraham, L., Körner, M., Schwab, P. & Hiersemann, M. (2004). Adv. Synth. Catal. 346, 1281–1294. Web of Science CSD CrossRef CAS Google Scholar
Corey, E. J. & Snider, B. B. (1972). J. Am. Chem. Soc. 94, 2549–2550. CrossRef CAS PubMed Web of Science Google Scholar
Evans, D. A., Bartroli, J. & Shih, T. L. (1981). J. Am. Chem. Soc. 103, 2127–2129. CrossRef CAS Web of Science Google Scholar
Evans, 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
Körner, M. & Hiersemann, M. (2006). Synlett, pp. 121–123. Google Scholar
Körner, M. & Hiersemann, M. (2007). Org. Lett. 9, 4979–4982. Web of Science PubMed Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr and R. M. Sweet, pp. 307–326, New York: Academic Press. Google Scholar
Pollex, A. & Hiersemann, M. (2005). Org. Lett. 7, 5705–5708. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 8| August 2008| Page o1517

doi:10.1107/S1600536808021181

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

(3R,4S,5S)-4-Hydr­­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]tetra­hydro­furan-2-one

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Experimental

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Data collection

Refinement

Supporting information

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organic compounds

(3R,4S,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]tetrahydrofuran-2-one