2-C-Cyclo-hexyl-2,3-O-isopropyl-idene-erythrofuran-ose.

In the title compound, C(13)H(22)O(4), the acetonide ring adopts an envelope conformation with one of the O atoms as the flap atom, whereas a twisted conformation is found for the furan-ose ring. Centrosymmetric eight-membered {⋯OCOH}(2) synthons involving the hydr-oxy H and acetonide O atoms are found in the crystal structure. These are linked into a supra-molecular chain in the a-axis direction via C-H⋯O contacts.

Related literature

For the dihydroxy­lation of the olefin portion of 1,2-dioxines, see: Robinson et al. (2006 ▶, 2009 ▶); Valente et al. (2009 ▶); Pedersen et al. (2009 ▶).

Experimental

Crystal data

C13H22O4

M = 242.31

Triclinic,

a = 5.454 (3) Å

b = 9.908 (3) Å

c = 12.442 (5) Å

α = 93.29 (3)°

β = 94.95 (4)°

γ = 102.94 (3)°

V = 650.8 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.24 × 0.15 × 0.13 mm

Data collection

Rigaku AFC12K/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.789, T max = 1

4992 measured reflections

2224 independent reflections

2064 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.124

S = 1.09

2224 reflections

156 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048557/hg2594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048557/hg2594Isup2.hkl

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

C13H22O4	Z = 2
Mr = 242.31	F(000) = 264
Triclinic, P1	Dx = 1.237 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.454 (3) Å	Cell parameters from 657 reflections
b = 9.908 (3) Å	θ = 2.1–30.2°
c = 12.442 (5) Å	µ = 0.09 mm−1
α = 93.29 (3)°	T = 153 K
β = 94.95 (4)°	Needle, colourless
γ = 102.94 (3)°	0.24 × 0.15 × 0.13 mm
V = 650.8 (5) Å3

Rigaku AFC12K/SATURN724 diffractometer	2224 independent reflections
Radiation source: fine-focus sealed tube	2064 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→5
Tmin = 0.789, Tmax = 1	k = −11→11
4992 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.066P)2 + 0.1734P] where P = (Fo2 + 2Fc2)/3
2224 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.69690 (18)	0.26256 (11)	0.70713 (8)	0.0281 (3)
O2	1.0523 (2)	0.34466 (12)	0.62499 (9)	0.0352 (3)
O3	0.9937 (2)	0.48884 (11)	0.85907 (9)	0.0377 (3)
O4	1.0310 (3)	0.31604 (12)	0.97416 (9)	0.0439 (4)
H4O	1.0281	0.3703	1.0282	0.066*
C1	0.7854 (3)	0.33328 (17)	0.61509 (12)	0.0312 (4)
C2	1.1367 (3)	0.33878 (16)	0.73567 (13)	0.0320 (4)
H2	1.2783	0.2898	0.7425	0.038*
C3	0.9031 (3)	0.25734 (15)	0.78511 (12)	0.0270 (4)
C4	0.8885 (3)	0.35109 (16)	0.88634 (12)	0.0327 (4)
H4	0.7088	0.3415	0.9019	0.039*
C5	1.2089 (3)	0.47939 (18)	0.80110 (15)	0.0410 (4)
H5A	1.3609	0.4853	0.8524	0.049*
H5B	1.2450	0.5556	0.7526	0.049*
C6	0.7237 (3)	0.47484 (18)	0.61632 (14)	0.0366 (4)
H6A	0.5397	0.4637	0.6085	0.055*
H6B	0.7959	0.5243	0.5562	0.055*
H6C	0.7954	0.5282	0.6850	0.055*
C7	0.6697 (4)	0.2440 (2)	0.51267 (14)	0.0446 (5)
H7A	0.4850	0.2278	0.5085	0.067*
H7B	0.7193	0.1549	0.5134	0.067*
H7C	0.7299	0.2916	0.4497	0.067*
C8	0.9010 (3)	0.10690 (15)	0.80714 (12)	0.0281 (4)
H8	1.0454	0.1086	0.8629	0.034*
C9	0.9368 (3)	0.01889 (16)	0.70736 (14)	0.0353 (4)
H9A	0.7968	0.0159	0.6504	0.042*
H9B	1.0973	0.0623	0.6788	0.042*
C10	0.9421 (3)	−0.12889 (17)	0.73441 (16)	0.0410 (4)
H10A	0.9581	−0.1844	0.6677	0.049*
H10B	1.0915	−0.1265	0.7863	0.049*
C11	0.7028 (3)	−0.19803 (17)	0.78331 (14)	0.0363 (4)
H11A	0.5557	−0.2117	0.7280	0.044*
H11B	0.7179	−0.2905	0.8053	0.044*
C12	0.6588 (3)	−0.11062 (17)	0.88099 (14)	0.0376 (4)
H12A	0.7936	−0.1083	0.9402	0.045*
H12B	0.4948	−0.1539	0.9067	0.045*
C13	0.6576 (3)	0.03762 (17)	0.85399 (13)	0.0343 (4)
H13A	0.6391	0.0929	0.9204	0.041*
H13B	0.5107	0.0361	0.8010	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0218 (5)	0.0379 (6)	0.0252 (6)	0.0082 (4)	0.0014 (4)	0.0048 (4)
O2	0.0277 (6)	0.0454 (7)	0.0345 (6)	0.0098 (5)	0.0089 (5)	0.0062 (5)
O3	0.0485 (7)	0.0307 (6)	0.0335 (7)	0.0112 (5)	−0.0019 (5)	−0.0002 (5)
O4	0.0662 (8)	0.0383 (7)	0.0279 (6)	0.0212 (6)	−0.0115 (6)	−0.0033 (5)
C1	0.0266 (8)	0.0414 (9)	0.0262 (8)	0.0078 (6)	0.0047 (6)	0.0051 (6)
C2	0.0240 (8)	0.0352 (8)	0.0373 (9)	0.0082 (6)	0.0009 (6)	0.0041 (7)
C3	0.0234 (7)	0.0332 (8)	0.0250 (8)	0.0095 (6)	−0.0009 (6)	−0.0001 (6)
C4	0.0413 (9)	0.0312 (8)	0.0264 (8)	0.0125 (7)	−0.0015 (7)	0.0008 (6)
C5	0.0334 (9)	0.0370 (9)	0.0483 (10)	0.0027 (7)	−0.0044 (7)	0.0023 (8)
C6	0.0343 (9)	0.0440 (10)	0.0337 (9)	0.0121 (7)	0.0037 (7)	0.0100 (7)
C7	0.0490 (11)	0.0548 (11)	0.0272 (9)	0.0082 (8)	−0.0003 (8)	0.0005 (8)
C8	0.0260 (8)	0.0313 (8)	0.0272 (8)	0.0084 (6)	0.0005 (6)	0.0000 (6)
C9	0.0347 (9)	0.0351 (9)	0.0373 (9)	0.0079 (7)	0.0124 (7)	−0.0006 (7)
C10	0.0407 (10)	0.0329 (9)	0.0506 (11)	0.0097 (7)	0.0137 (8)	−0.0047 (7)
C11	0.0380 (9)	0.0314 (8)	0.0378 (9)	0.0050 (7)	0.0042 (7)	−0.0006 (7)
C12	0.0432 (10)	0.0365 (9)	0.0340 (9)	0.0088 (7)	0.0070 (7)	0.0061 (7)
C13	0.0369 (9)	0.0369 (9)	0.0319 (9)	0.0119 (7)	0.0107 (7)	0.0027 (7)

O1—C3	1.4328 (18)	C7—H7A	0.9800
O1—C1	1.4392 (19)	C7—H7B	0.9800
O2—C2	1.423 (2)	C7—H7C	0.9800
O2—C1	1.429 (2)	C8—C9	1.528 (2)
O3—C4	1.429 (2)	C8—C13	1.531 (2)
O3—C5	1.447 (2)	C8—H8	1.0000
O4—C4	1.392 (2)	C9—C10	1.527 (2)
O4—H4O	0.8399	C9—H9A	0.9900
C1—C7	1.512 (2)	C9—H9B	0.9900
C1—C6	1.513 (2)	C10—C11	1.526 (2)
C2—C5	1.526 (2)	C10—H10A	0.9900
C2—C3	1.544 (2)	C10—H10B	0.9900
C2—H2	1.0000	C11—C12	1.519 (2)
C3—C8	1.529 (2)	C11—H11A	0.9900
C3—C4	1.540 (2)	C11—H11B	0.9900
C4—H4	1.0000	C12—C13	1.527 (2)
C5—H5A	0.9900	C12—H12A	0.9900
C5—H5B	0.9900	C12—H12B	0.9900
C6—H6A	0.9800	C13—H13A	0.9900
C6—H6B	0.9800	C13—H13B	0.9900
C6—H6C	0.9800
C3—O1—C1	111.24 (11)	C1—C7—H7B	109.5
C2—O2—C1	108.79 (12)	H7A—C7—H7B	109.5
C4—O3—C5	105.95 (12)	C1—C7—H7C	109.5
C4—O4—H4O	108.8	H7A—C7—H7C	109.5
O2—C1—O1	105.26 (12)	H7B—C7—H7C	109.5
O2—C1—C7	108.62 (14)	C9—C8—C3	113.25 (13)
O1—C1—C7	109.15 (13)	C9—C8—C13	109.62 (13)
O2—C1—C6	111.35 (13)	C3—C8—C13	111.20 (12)
O1—C1—C6	110.47 (13)	C9—C8—H8	107.5
C7—C1—C6	111.76 (14)	C3—C8—H8	107.5
O2—C2—C5	114.39 (14)	C13—C8—H8	107.5
O2—C2—C3	104.95 (12)	C10—C9—C8	111.22 (14)
C5—C2—C3	104.74 (13)	C10—C9—H9A	109.4
O2—C2—H2	110.8	C8—C9—H9A	109.4
C5—C2—H2	110.8	C10—C9—H9B	109.4
C3—C2—H2	110.8	C8—C9—H9B	109.4
O1—C3—C8	110.40 (12)	H9A—C9—H9B	108.0
O1—C3—C4	108.10 (12)	C11—C10—C9	111.32 (14)
C8—C3—C4	114.24 (13)	C11—C10—H10A	109.4
O1—C3—C2	103.39 (12)	C9—C10—H10A	109.4
C8—C3—C2	116.55 (12)	C11—C10—H10B	109.4
C4—C3—C2	103.27 (12)	C9—C10—H10B	109.4
O4—C4—O3	111.08 (13)	H10A—C10—H10B	108.0
O4—C4—C3	109.45 (12)	C12—C11—C10	111.32 (14)
O3—C4—C3	104.59 (13)	C12—C11—H11A	109.4
O4—C4—H4	110.5	C10—C11—H11A	109.4
O3—C4—H4	110.5	C12—C11—H11B	109.4
C3—C4—H4	110.5	C10—C11—H11B	109.4
O3—C5—C2	106.01 (13)	H11A—C11—H11B	108.0
O3—C5—H5A	110.5	C11—C12—C13	111.60 (14)
C2—C5—H5A	110.5	C11—C12—H12A	109.3
O3—C5—H5B	110.5	C13—C12—H12A	109.3
C2—C5—H5B	110.5	C11—C12—H12B	109.3
H5A—C5—H5B	108.7	C13—C12—H12B	109.3
C1—C6—H6A	109.5	H12A—C12—H12B	108.0
C1—C6—H6B	109.5	C12—C13—C8	111.60 (13)
H6A—C6—H6B	109.5	C12—C13—H13A	109.3
C1—C6—H6C	109.5	C8—C13—H13A	109.3
H6A—C6—H6C	109.5	C12—C13—H13B	109.3
H6B—C6—H6C	109.5	C8—C13—H13B	109.3
C1—C7—H7A	109.5	H13A—C13—H13B	108.0
C2—O2—C1—O1	−24.16 (15)	C2—C3—C4—O4	−89.45 (15)
C2—O2—C1—C7	−140.95 (13)	O1—C3—C4—O3	−79.48 (14)
C2—O2—C1—C6	95.56 (15)	C8—C3—C4—O3	157.20 (12)
C3—O1—C1—O2	12.78 (15)	C2—C3—C4—O3	29.63 (14)
C3—O1—C1—C7	129.21 (14)	C4—O3—C5—C2	34.96 (16)
C3—O1—C1—C6	−107.53 (14)	O2—C2—C5—O3	99.37 (16)
C1—O2—C2—C5	−88.63 (16)	C3—C2—C5—O3	−14.97 (16)
C1—O2—C2—C3	25.58 (15)	O1—C3—C8—C9	62.51 (16)
C1—O1—C3—C8	−122.93 (13)	C4—C3—C8—C9	−175.42 (12)
C1—O1—C3—C4	111.46 (14)	C2—C3—C8—C9	−55.00 (17)
C1—O1—C3—C2	2.43 (14)	O1—C3—C8—C13	−61.44 (16)
O2—C2—C3—O1	−16.78 (14)	C4—C3—C8—C13	60.62 (17)
C5—C2—C3—O1	104.03 (13)	C2—C3—C8—C13	−178.95 (12)
O2—C2—C3—C8	104.51 (14)	C3—C8—C9—C10	178.09 (12)
C5—C2—C3—C8	−134.68 (14)	C13—C8—C9—C10	−57.09 (17)
O2—C2—C3—C4	−129.38 (12)	C8—C9—C10—C11	56.64 (19)
C5—C2—C3—C4	−8.57 (15)	C9—C10—C11—C12	−54.5 (2)
C5—O3—C4—O4	77.45 (16)	C10—C11—C12—C13	53.94 (19)
C5—O3—C4—C3	−40.52 (15)	C11—C12—C13—C8	−55.52 (18)
O1—C3—C4—O4	161.44 (12)	C9—C8—C13—C12	56.55 (17)
C8—C3—C4—O4	38.13 (18)	C3—C8—C13—C12	−177.46 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H40···O3i	0.84	1.95	2.787 (2)	173
C2—H2···O1ii	1.00	2.43	3.350 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H40⋯O3i	0.84	1.95	2.787 (2)	173
C2—H2⋯O1ii	1.00	2.43	3.350 (3)	152

Symmetry codes: (i) ; (ii) .