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

The title compound, C(11)H(18)O(3), was synthesized to prove the relative configuration of the corresponding acyclic C1-C8 stereopentade. Mol-ecules are linked via O-H⋯O hydrogen bonds, forming a chain along the b axis.

Related literature

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

Experimental

Crystal data

C11H18O3

M = 198.25

Orthorhombic,

a = 5.4414 (14) Å

b = 10.132 (2) Å

c = 20.975 (8) Å

V = 1156.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 291 (1) K

0.36 × 0.06 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

7554 measured reflections

1223 independent reflections

346 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.087

S = 0.97

1223 reflections

131 parameters

H-atom parameters constrained

Δρmax = 0.09 e Å−3

Δρmin = −0.13 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026998/bt2768sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026998/bt2768Isup2.hkl

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

C11H18O3	F000 = 432
Mr = 198.25	Dx = 1.139 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7554 reflections
a = 5.4414 (14) Å	θ = 2.8–25.0º
b = 10.132 (2) Å	µ = 0.08 mm−1
c = 20.975 (8) Å	T = 291 (1) K
V = 1156.4 (6) Å3	Needle, colourless
Z = 4	0.36 × 0.06 × 0.02 mm

Nonius KappaCCD diffractometer	1223 independent reflections
Radiation source: fine-focus sealed tube	346 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.048
Detector resolution: 19 vertical, 18 horizontal pixels mm-1	θmax = 25.0º
T = 291(1) K	θmin = 2.8º
111 frames via ω–rotation (Δω=2%) and two times 180 s per frame (three sets at different κ–angles) scans	h = −6→6
Absorption correction: none	k = −12→12
7554 measured reflections	l = −24→24

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) = 0.087	[1.0 exp(5.65(sinθ/λ)2)]/[σ2(Fo2)]
S = 0.97	(Δ/σ)max = 0.007
1223 reflections	Δρmax = 0.09 e Å−3
131 parameters	Δρmin = −0.13 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.1778 (7)	0.0092 (4)	−0.3153 (2)	0.0647 (11)
O2	0.4408 (8)	0.0462 (4)	−0.2370 (2)	0.0971 (19)
O3	0.3095 (10)	−0.2710 (5)	−0.3391 (2)	0.0890 (15)
H3	0.4090	−0.3080	−0.3158	0.133*
C1	0.2948 (12)	−0.0261 (7)	−0.2615 (3)	0.075 (2)
C2	0.2076 (11)	−0.1595 (6)	−0.2396 (3)	0.0641 (19)
H2A	0.3449	−0.2114	−0.2227	0.077*
C3	0.1142 (11)	−0.2191 (6)	−0.3017 (3)	0.0635 (19)
H3B	−0.0147	−0.2849	−0.2942	0.076*
C4	0.0156 (11)	−0.0982 (5)	−0.3372 (3)	0.0596 (18)
H4A	−0.1522	−0.0803	−0.3227	0.072*
C5	0.0176 (10)	−0.1020 (6)	−0.4090 (3)	0.0578 (17)
H5A	0.1854	−0.1235	−0.4225	0.069*
C6	−0.0502 (11)	0.0338 (6)	−0.4390 (3)	0.069 (2)
H6A	0.0627	0.0986	−0.4205	0.082*
C7	0.0064 (15)	0.0286 (7)	−0.5094 (4)	0.107 (3)
H7A	0.1591	−0.0070	−0.5193	0.129*
C8	−0.1131 (18)	0.0629 (9)	−0.5549 (4)	0.170 (4)
H8A	−0.2681	0.0996	−0.5491	0.205*
H8B	−0.0501	0.0527	−0.5958	0.205*
C9	0.0066 (12)	−0.1412 (5)	−0.1883 (3)	0.093 (2)
H9A	−0.0491	−0.2261	−0.1740	0.140*
H9B	−0.1291	−0.0932	−0.2062	0.140*
H9C	0.0731	−0.0929	−0.1529	0.140*
C10	−0.1534 (11)	−0.2165 (5)	−0.4322 (3)	0.085 (2)
H10A	−0.0821	−0.2998	−0.4207	0.128*
H10B	−0.1712	−0.2119	−0.4777	0.128*
H10C	−0.3118	−0.2079	−0.4125	0.128*
C11	−0.3096 (12)	0.0798 (6)	−0.4222 (3)	0.102 (3)
H11A	−0.3376	0.1657	−0.4401	0.152*
H11B	−0.3269	0.0840	−0.3767	0.152*
H11C	−0.4273	0.0187	−0.4393	0.152*

	U11	U22	U33	U12	U13	U23
O1	0.064 (3)	0.056 (3)	0.074 (3)	−0.002 (3)	−0.011 (3)	−0.006 (2)
O2	0.091 (4)	0.110 (4)	0.091 (4)	−0.027 (3)	−0.026 (3)	−0.012 (3)
O3	0.105 (4)	0.080 (3)	0.083 (3)	0.034 (3)	0.005 (3)	0.002 (3)
C1	0.062 (6)	0.083 (6)	0.081 (6)	0.010 (5)	−0.004 (5)	−0.010 (5)
C2	0.073 (5)	0.065 (5)	0.054 (5)	0.008 (4)	−0.013 (4)	0.009 (3)
C3	0.072 (5)	0.048 (4)	0.071 (5)	0.000 (4)	0.009 (4)	0.005 (4)
C4	0.053 (5)	0.056 (4)	0.070 (5)	0.000 (4)	0.002 (4)	−0.006 (4)
C5	0.039 (4)	0.068 (4)	0.066 (5)	0.001 (4)	−0.002 (4)	−0.008 (4)
C6	0.072 (6)	0.073 (4)	0.061 (5)	0.005 (4)	−0.013 (4)	0.009 (4)
C7	0.133 (7)	0.106 (6)	0.082 (7)	0.050 (6)	−0.028 (6)	0.007 (5)
C8	0.233 (13)	0.159 (9)	0.119 (10)	−0.006 (8)	−0.019 (9)	0.019 (7)
C9	0.119 (7)	0.089 (5)	0.071 (6)	0.002 (5)	0.021 (6)	0.004 (4)
C10	0.094 (6)	0.078 (5)	0.084 (5)	−0.016 (4)	−0.015 (5)	−0.013 (4)
C11	0.085 (6)	0.111 (6)	0.109 (6)	0.048 (5)	0.007 (5)	0.021 (4)

O1—C1	1.344 (6)	C6—C7	1.508 (8)
O1—C4	1.475 (6)	C6—C11	1.527 (6)
O2—C1	1.196 (6)	C6—H6A	0.9800
O3—C3	1.422 (6)	C7—C8	1.207 (8)
O3—H3	0.8200	C7—H7A	0.9300
C1—C2	1.504 (7)	C8—H8A	0.9300
C2—C3	1.523 (7)	C8—H8B	0.9300
C2—C9	1.546 (7)	C9—H9A	0.9600
C2—H2A	0.9800	C9—H9B	0.9600
C3—C4	1.531 (6)	C9—H9C	0.9600
C3—H3B	0.9800	C10—H10A	0.9600
C4—C5	1.506 (6)	C10—H10B	0.9600
C4—H4A	0.9800	C10—H10C	0.9600
C5—C6	1.557 (6)	C11—H11A	0.9600
C5—C10	1.564 (7)	C11—H11B	0.9600
C5—H5A	0.9800	C11—H11C	0.9600
C1—O1—C4	110.5 (5)	C7—C6—C5	108.4 (5)
C3—O3—H3	109.5	C11—C6—C5	113.3 (5)
O2—C1—O1	120.8 (7)	C7—C6—H6A	106.5
O2—C1—C2	129.0 (7)	C11—C6—H6A	106.5
O1—C1—C2	110.2 (6)	C5—C6—H6A	106.5
C1—C2—C3	101.6 (5)	C8—C7—C6	130.9 (9)
C1—C2—C9	109.1 (5)	C8—C7—H7A	114.6
C3—C2—C9	114.0 (6)	C6—C7—H7A	114.6
C1—C2—H2A	110.6	C7—C8—H8A	120.0
C3—C2—H2A	110.6	C7—C8—H8B	120.0
C9—C2—H2A	110.6	H8A—C8—H8B	120.0
O3—C3—C2	111.7 (5)	C2—C9—H9A	109.5
O3—C3—C4	106.8 (5)	C2—C9—H9B	109.5
C2—C3—C4	102.5 (5)	H9A—C9—H9B	109.5
O3—C3—H3B	111.8	C2—C9—H9C	109.5
C2—C3—H3B	111.8	H9A—C9—H9C	109.5
C4—C3—H3B	111.8	H9B—C9—H9C	109.5
O1—C4—C5	109.1 (5)	C5—C10—H10A	109.5
O1—C4—C3	103.2 (4)	C5—C10—H10B	109.5
C5—C4—C3	117.6 (5)	H10A—C10—H10B	109.5
O1—C4—H4A	108.8	C5—C10—H10C	109.5
C5—C4—H4A	108.8	H10A—C10—H10C	109.5
C3—C4—H4A	108.8	H10B—C10—H10C	109.5
C4—C5—C6	112.3 (5)	C6—C11—H11A	109.5
C4—C5—C10	109.0 (5)	C6—C11—H11B	109.5
C6—C5—C10	112.8 (5)	H11A—C11—H11B	109.5
C4—C5—H5A	107.5	C6—C11—H11C	109.5
C6—C5—H5A	107.5	H11A—C11—H11C	109.5
C10—C5—H5A	107.5	H11B—C11—H11C	109.5
C7—C6—C11	115.1 (5)
C4—O1—C1—O2	177.8 (6)	C2—C3—C4—O1	31.7 (6)
C4—O1—C1—C2	−3.8 (7)	O3—C3—C4—C5	34.3 (8)
O2—C1—C2—C3	−157.8 (7)	C2—C3—C4—C5	151.8 (5)
O1—C1—C2—C3	24.0 (7)	O1—C4—C5—C6	−54.5 (6)
O2—C1—C2—C9	81.5 (9)	C3—C4—C5—C6	−171.5 (5)
O1—C1—C2—C9	−96.7 (6)	O1—C4—C5—C10	179.7 (5)
C1—C2—C3—O3	80.8 (6)	C3—C4—C5—C10	62.7 (7)
C9—C2—C3—O3	−162.0 (5)	C4—C5—C6—C7	168.6 (6)
C1—C2—C3—C4	−33.2 (6)	C10—C5—C6—C7	−67.7 (7)
C9—C2—C3—C4	84.0 (6)	C4—C5—C6—C11	−62.3 (7)
C1—O1—C4—C5	−143.8 (5)	C10—C5—C6—C11	61.4 (7)
C1—O1—C4—C3	−18.0 (6)	C11—C6—C7—C8	5.6 (14)
O3—C3—C4—O1	−85.8 (5)	C5—C6—C7—C8	133.7 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.82	2.02	2.798 (6)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.82	2.02	2.798 (6)	158

Symmetry code: (i) .