(3S,4S,5R)-4-Hydr-oxy-3-methyl-5-[(2S,3R)-3-methyl-pent-4-en-2-yl]-4,5-dihydro-furan-2(3H)-one.

The relative configuration of the title compound, C(11)H(18)O(3), was corroborated by single-crystal X-ray diffraction analysis. In the crystal, mol-ecules are linked via a O-H⋯O hydrogen bond and a chain of mol-ecules is formed along [010].

Related literature

For further synthetic details, see: Abraham, Körner & Hierse­mann (2004 ▶); Abraham, Körner et al. (2004 ▶); Evans et al. (1981 ▶, 1999 ▶); Körner & Hiersemann (2006 ▶, 2007 ▶); Mitsunobu (1981 ▶); Mitsunobu & Yamada (1967 ▶); Mitsunobu et al. (1967 ▶); Otera et al. (1992 ▶); Pollex & Hiersemann (2005 ▶).

Experimental

Crystal data

C11H18O3

M = 198.25

Monoclinic,

a = 7.604 (2) Å

b = 6.574 (2) Å

c = 11.323 (4) Å

β = 91.211 (7)°

V = 565.9 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 173 (2) K

0.35 × 0.10 × 0.07 mm

Data collection

Siemens SMART three-axis goniometer with APEXII area-detector diffractometer

Absorption correction: none

7868 measured reflections

1507 independent reflections

1076 reflections with I > 2σ(I)

R int = 0.131

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.098

S = 0.98

1507 reflections

132 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042414/hb2861sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042414/hb2861Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H18O3	F(000) = 216
Mr = 198.25	Dx = 1.163 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1365 reflections
a = 7.604 (2) Å	θ = 2.7–26.3°
b = 6.574 (2) Å	µ = 0.08 mm−1
c = 11.323 (4) Å	T = 173 K
β = 91.211 (7)°	Needle, colourless
V = 565.9 (3) Å3	0.35 × 0.10 × 0.07 mm
Z = 2

Siemens SMART three-axis goniometer with APEXII area-detector system diffractometer	1076 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.131
graphite	θmax = 28.3°, θmin = 1.8°
Detector resolution: 512 pixels mm-1	h = −9→10
Data collection strategy APEX 2/COSMO scans	k = −8→8
7868 measured reflections	l = −15→14
1507 independent reflections

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0279P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
1507 reflections	Δρmax = 0.19 e Å−3
132 parameters	Δρmin = −0.19 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: 0.077 (11)

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.

	x	y	z	Uiso*/Ueq
O1	0.2255 (2)	0.2085 (3)	0.91883 (16)	0.0351 (5)
O2	0.1493 (2)	0.7353 (3)	0.96072 (16)	0.0382 (5)
H2	0.2076	0.8318	0.9904	0.057*
O3	0.2839 (2)	0.0670 (3)	1.09375 (17)	0.0408 (5)
C1	0.3186 (5)	0.7143 (7)	0.4846 (3)	0.0700 (11)
H1A	0.1994	0.7345	0.4607	0.084*
H1B	0.4096	0.7302	0.4292	0.084*
C2	0.3570 (4)	0.6651 (5)	0.5929 (3)	0.0471 (8)
H2A	0.4783	0.6469	0.6118	0.057*
C3	0.2316 (4)	0.6337 (4)	0.6919 (2)	0.0381 (7)
H3	0.2615	0.7378	0.7535	0.046*
C4	0.2658 (4)	0.4224 (4)	0.7492 (2)	0.0352 (7)
H4	0.3959	0.4082	0.7615	0.042*
C5	0.1827 (3)	0.4084 (4)	0.8699 (2)	0.0305 (6)
H5	0.0522	0.4226	0.8610	0.037*
C6	0.2512 (3)	0.5554 (4)	0.9651 (2)	0.0309 (6)
H6	0.3778	0.5877	0.9522	0.037*
C7	0.2319 (4)	0.4339 (4)	1.0786 (2)	0.0324 (6)
H7	0.1086	0.4522	1.1059	0.039*
C8	0.2500 (3)	0.2207 (4)	1.0367 (2)	0.0327 (6)
C9	0.0401 (4)	0.6683 (5)	0.6558 (3)	0.0513 (8)
H9A	0.0246	0.8089	0.6288	0.077*
H9B	−0.0348	0.6434	0.7236	0.077*
H9C	0.0072	0.5748	0.5916	0.077*
C10	0.2046 (4)	0.2460 (5)	0.6698 (3)	0.0468 (8)
H10A	0.2487	0.1173	0.7025	0.070*
H10B	0.2503	0.2650	0.5902	0.070*
H10C	0.0758	0.2429	0.6657	0.070*
C11	0.3561 (4)	0.4916 (5)	1.1806 (3)	0.0477 (8)
H11A	0.3352	0.4020	1.2481	0.071*
H11B	0.3347	0.6331	1.2035	0.071*
H11C	0.4781	0.4767	1.1558	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.0416 (11)	0.0232 (11)	0.0406 (11)	0.0024 (9)	0.0034 (8)	−0.0022 (8)
O2	0.0413 (11)	0.0230 (10)	0.0504 (12)	0.0052 (9)	0.0008 (9)	−0.0046 (9)
O3	0.0428 (12)	0.0276 (11)	0.0520 (13)	0.0029 (9)	0.0009 (10)	0.0033 (9)
C1	0.078 (2)	0.083 (3)	0.050 (2)	−0.008 (2)	0.0124 (17)	0.006 (2)
C2	0.0516 (19)	0.0459 (19)	0.0439 (19)	−0.0065 (15)	0.0038 (15)	−0.0007 (14)
C3	0.0457 (18)	0.0296 (15)	0.0391 (17)	−0.0013 (13)	0.0026 (14)	−0.0019 (12)
C4	0.0367 (16)	0.0273 (15)	0.0418 (16)	0.0022 (13)	0.0027 (12)	−0.0043 (13)
C5	0.0327 (14)	0.0184 (13)	0.0403 (16)	−0.0005 (12)	0.0005 (12)	−0.0025 (12)
C6	0.0294 (15)	0.0194 (14)	0.0441 (16)	−0.0010 (11)	0.0024 (12)	−0.0012 (12)
C7	0.0328 (15)	0.0250 (14)	0.0396 (16)	−0.0016 (12)	0.0010 (12)	−0.0060 (12)
C8	0.0275 (14)	0.0268 (14)	0.0440 (17)	−0.0030 (12)	0.0027 (12)	−0.0020 (14)
C9	0.057 (2)	0.0446 (19)	0.0527 (19)	0.0102 (16)	0.0027 (15)	0.0093 (14)
C10	0.066 (2)	0.0294 (16)	0.0447 (17)	0.0034 (16)	−0.0029 (15)	−0.0096 (14)
C11	0.054 (2)	0.0397 (17)	0.0489 (19)	−0.0075 (15)	−0.0091 (15)	0.0000 (14)

O1—C8	1.347 (3)	C5—C6	1.531 (4)
O1—C5	1.460 (3)	C5—H5	1.0000
O2—C6	1.414 (3)	C6—C7	1.522 (4)
O2—H2	0.8400	C6—H6	1.0000
O3—C8	1.223 (3)	C7—C8	1.487 (4)
C1—C2	1.296 (4)	C7—C11	1.524 (4)
C1—H1A	0.9500	C7—H7	1.0000
C1—H1B	0.9500	C9—H9A	0.9800
C2—C3	1.501 (4)	C9—H9B	0.9800
C2—H2A	0.9500	C9—H9C	0.9800
C3—C9	1.521 (4)	C10—H10A	0.9800
C3—C4	1.553 (4)	C10—H10B	0.9800
C3—H3	1.0000	C10—H10C	0.9800
C4—C5	1.520 (4)	C11—H11A	0.9800
C4—C10	1.534 (4)	C11—H11B	0.9800
C4—H4	1.0000	C11—H11C	0.9800
C8—O1—C5	110.4 (2)	C7—C6—H6	110.2
C6—O2—H2	109.5	C5—C6—H6	110.2
C2—C1—H1A	120.0	C8—C7—C6	102.4 (2)
C2—C1—H1B	120.0	C8—C7—C11	114.6 (2)
H1A—C1—H1B	120.0	C6—C7—C11	116.1 (2)
C1—C2—C3	127.4 (3)	C8—C7—H7	107.8
C1—C2—H2A	116.3	C6—C7—H7	107.8
C3—C2—H2A	116.3	C11—C7—H7	107.8
C2—C3—C9	113.5 (2)	O3—C8—O1	119.8 (3)
C2—C3—C4	109.4 (2)	O3—C8—C7	129.1 (2)
C9—C3—C4	113.4 (2)	O1—C8—C7	111.1 (2)
C2—C3—H3	106.7	C3—C9—H9A	109.5
C9—C3—H3	106.7	C3—C9—H9B	109.5
C4—C3—H3	106.7	H9A—C9—H9B	109.5
C5—C4—C10	110.8 (2)	C3—C9—H9C	109.5
C5—C4—C3	111.1 (2)	H9A—C9—H9C	109.5
C10—C4—C3	112.7 (2)	H9B—C9—H9C	109.5
C5—C4—H4	107.3	C4—C10—H10A	109.5
C10—C4—H4	107.3	C4—C10—H10B	109.5
C3—C4—H4	107.3	H10A—C10—H10B	109.5
O1—C5—C4	107.56 (19)	C4—C10—H10C	109.5
O1—C5—C6	103.3 (2)	H10A—C10—H10C	109.5
C4—C5—C6	117.0 (2)	H10B—C10—H10C	109.5
O1—C5—H5	109.5	C7—C11—H11A	109.5
C4—C5—H5	109.5	C7—C11—H11B	109.5
C6—C5—H5	109.5	H11A—C11—H11B	109.5
O2—C6—C7	113.9 (2)	C7—C11—H11C	109.5
O2—C6—C5	109.0 (2)	H11A—C11—H11C	109.5
C7—C6—C5	103.1 (2)	H11B—C11—H11C	109.5
O2—C6—H6	110.2
C1—C2—C3—C9	−0.8 (5)	C4—C5—C6—O2	90.6 (3)
C1—C2—C3—C4	126.9 (4)	O1—C5—C6—C7	−30.1 (2)
C2—C3—C4—C5	163.2 (2)	C4—C5—C6—C7	−148.1 (2)
C9—C3—C4—C5	−69.1 (3)	O2—C6—C7—C8	146.5 (2)
C2—C3—C4—C10	−71.8 (3)	C5—C6—C7—C8	28.6 (3)
C9—C3—C4—C10	55.9 (3)	O2—C6—C7—C11	−88.0 (3)
C8—O1—C5—C4	144.9 (2)	C5—C6—C7—C11	154.1 (2)
C8—O1—C5—C6	20.6 (2)	C5—O1—C8—O3	178.6 (2)
C10—C4—C5—O1	55.7 (3)	C5—O1—C8—C7	−2.0 (3)
C3—C4—C5—O1	−178.3 (2)	C6—C7—C8—O3	161.8 (3)
C10—C4—C5—C6	171.3 (2)	C11—C7—C8—O3	35.3 (4)
C3—C4—C5—C6	−62.6 (3)	C6—C7—C8—O1	−17.5 (3)
O1—C5—C6—O2	−151.49 (19)	C11—C7—C8—O1	−144.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.84	2.02	2.830 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.84	2.02	2.830 (3)	163

Symmetry code: (i) .