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

The title compound, C(11)H(18)O(3), was synthesized to prove the relative configuration of the corresponding acyclic C1-C8 stereopentade. It crystallizes with two mol-ecules in the asymmetric unit, which show only slight differences. The mol-ecules are linked via O-H⋯O hydrogen bonds, resulting in two crystallographically independent chains of mol-ecules 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 = 198.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.080

S = 1.06

2268 reflections

262 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.10 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/S1600536808021181/hb2741sup1.cif

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

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

C11H18O3	F000 = 432
Mr = 198.25	Dx = 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 = 3.0–25.4º
b = 16.411 (3) Å	µ = 0.08 mm−1
c = 11.607 (2) Å	T = 291 (1) K
β = 95.46 (3)º	Block, colourless
V = 1193.4 (4) Å3	0.30 × 0.28 × 0.20 mm
Z = 4

Nonius KappaCCD diffractometer	2268 independent reflections
Radiation source: fine-focus sealed tube	1228 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 19 vertical, 18 horizontal pixels mm-1	θmax = 25.4º
T = 291(1) K	θmin = 3.0º
259 frames via ω–rotation (Δω=1%) and two times 120 s per frame (three sets at different κ–angles) scans	h = −7→7
Absorption correction: none	k = −19→19
9263 measured reflections	l = −13→13

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(Fo2) + (0.0276P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2268 reflections	Δρmax = 0.14 e Å−3
262 parameters	Δρmin = −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)

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	−0.2547 (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*

	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)

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)

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

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) .