1,2,3-Tri-O-acetyl-5-de-oxy-d-ribofuran-ose.

The title compound, C(11)H(16)O(7), was obtained from the breakage reaction of the glycosidic bond of 5'-de-oxy-2',3'-diacetyl-inosine. The ribofuran-ose ring has a C2-exo, C3-endo twist configuration. No alteration of the relative configuration compared with d-(-)-ribose is observed.

Related literature

For possible catalytic mechanisms at the anomeric carbon centre in the cleavage of glycosidic linkages, see: Vocadlo et al. (2001 ▶). For the synthesis of the title compound from d-ribose, see: Sairam et al. (2003 ▶). For a 5-de­oxy-ribofuran­oid active as an anti­tumour drug, see: Shimma et al. (2000 ▶).

Experimental

Crystal data

C11H16O7

M = 260.24

Orthorhombic,

a = 7.592 (2) Å

b = 8.505 (2) Å

c = 20.445 (2) Å

V = 1320.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.48 × 0.45 × 0.32 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.949, T max = 0.966

5470 measured reflections

1368 independent reflections

848 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.133

S = 1.04

1368 reflections

168 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004482X/si2303sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004482X/si2303Isup2.hkl

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

C11H16O7	Dx = 1.309 Mg m−3
Mr = 260.24	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1390 reflections
a = 7.592 (2) Å	θ = 2.6–21.6°
b = 8.505 (2) Å	µ = 0.11 mm−1
c = 20.445 (2) Å	T = 298 K
V = 1320.1 (5) Å3	Prism, colourless
Z = 4	0.48 × 0.45 × 0.32 mm
F(000) = 552

Siemens SMART 1000 CCD area-detector diffractometer	1368 independent reflections
Radiation source: fine-focus sealed tube	848 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.949, Tmax = 0.966	k = −10→9
5470 measured reflections	l = −24→11

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.2525P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1368 reflections	Δρmax = 0.18 e Å−3
168 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (4)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.1176 (4)	0.2987 (4)	0.07061 (14)	0.0875 (10)
O2	0.2931 (4)	0.3413 (4)	0.16197 (14)	0.0848 (10)
O3	0.4083 (8)	0.5348 (6)	0.1051 (2)	0.162 (2)
O4	0.2959 (4)	−0.0158 (4)	0.07017 (13)	0.0873 (11)
O5	0.5372 (5)	−0.0822 (5)	0.1230 (2)	0.1261 (16)
O6	−0.0276 (4)	−0.0744 (3)	0.12588 (12)	0.0711 (9)
O7	0.0619 (5)	−0.1341 (4)	0.22641 (13)	0.0952 (12)
C1	0.2710 (6)	0.2524 (6)	0.1032 (2)	0.0750 (13)
H1	0.3742	0.2633	0.0748	0.090*
C2	0.2469 (6)	0.0844 (6)	0.12401 (18)	0.0695 (12)
H2	0.3104	0.0591	0.1644	0.083*
C3	0.0506 (6)	0.0772 (5)	0.13214 (17)	0.0628 (11)
H3	0.0192	0.1214	0.1748	0.075*
C4	−0.0187 (6)	0.1839 (5)	0.07907 (19)	0.0678 (11)
H4	−0.0317	0.1235	0.0385	0.081*
C5	−0.1893 (6)	0.2655 (5)	0.0940 (2)	0.0917 (16)
H5A	−0.1762	0.3274	0.1330	0.138*
H5B	−0.2802	0.1886	0.1005	0.138*
H5C	−0.2206	0.3327	0.0581	0.138*
C6	0.3685 (7)	0.4813 (7)	0.1569 (3)	0.0917 (15)
C7	0.3865 (8)	0.5618 (7)	0.2211 (3)	0.1153 (19)
H7A	0.4613	0.5007	0.2492	0.173*
H7B	0.2725	0.5726	0.2409	0.173*
H7C	0.4374	0.6639	0.2146	0.173*
C8	0.4508 (7)	−0.0888 (6)	0.0750 (2)	0.0784 (13)
C9	0.4968 (8)	−0.1728 (7)	0.0142 (2)	0.111 (2)
H9A	0.5860	−0.1152	−0.0088	0.166*
H9B	0.3940	−0.1822	−0.0128	0.166*
H9C	0.5403	−0.2757	0.0248	0.166*
C10	−0.0159 (6)	−0.1698 (5)	0.1781 (2)	0.0681 (11)
C11	−0.1095 (8)	−0.3204 (6)	0.1666 (2)	0.0968 (16)
H11A	−0.0379	−0.3877	0.1399	0.145*
H11B	−0.2191	−0.3001	0.1448	0.145*
H11C	−0.1320	−0.3709	0.2078	0.145*

	U11	U22	U33	U12	U13	U23
O1	0.090 (2)	0.087 (2)	0.086 (2)	−0.018 (2)	−0.0159 (18)	0.0309 (18)
O2	0.095 (2)	0.089 (2)	0.0703 (19)	−0.023 (2)	−0.0001 (17)	0.0068 (19)
O3	0.232 (6)	0.137 (4)	0.116 (3)	−0.093 (4)	0.011 (4)	0.022 (3)
O4	0.087 (2)	0.115 (3)	0.0599 (17)	0.025 (2)	−0.0058 (16)	−0.0044 (18)
O5	0.099 (3)	0.135 (4)	0.145 (3)	0.029 (3)	−0.043 (3)	−0.031 (3)
O6	0.098 (2)	0.0548 (17)	0.0604 (16)	−0.0068 (19)	−0.0069 (15)	0.0085 (14)
O7	0.148 (3)	0.079 (2)	0.0585 (17)	−0.009 (2)	−0.0165 (19)	0.0096 (16)
C1	0.070 (3)	0.095 (4)	0.060 (2)	−0.010 (3)	0.000 (2)	0.004 (2)
C2	0.073 (3)	0.088 (3)	0.048 (2)	0.006 (3)	−0.006 (2)	0.001 (2)
C3	0.077 (3)	0.062 (3)	0.050 (2)	0.001 (3)	−0.0017 (19)	0.010 (2)
C4	0.077 (3)	0.064 (2)	0.062 (2)	−0.008 (3)	−0.012 (2)	0.010 (2)
C5	0.081 (3)	0.074 (3)	0.120 (4)	0.003 (3)	−0.013 (3)	0.016 (3)
C6	0.100 (4)	0.086 (4)	0.089 (4)	−0.024 (3)	−0.009 (3)	0.015 (3)
C7	0.132 (5)	0.101 (4)	0.112 (4)	−0.019 (4)	−0.028 (4)	−0.003 (4)
C8	0.073 (3)	0.076 (3)	0.086 (3)	−0.002 (3)	0.005 (3)	0.007 (3)
C9	0.118 (4)	0.113 (4)	0.102 (4)	0.007 (4)	0.030 (3)	0.008 (4)
C10	0.086 (3)	0.062 (3)	0.057 (2)	0.009 (3)	0.006 (2)	0.011 (2)
C11	0.135 (4)	0.067 (3)	0.088 (3)	−0.015 (3)	−0.014 (3)	0.018 (3)

O1—C1	1.399 (5)	C4—C5	1.501 (6)
O1—C4	1.433 (5)	C4—H4	0.9800
O2—C6	1.325 (6)	C5—H5A	0.9600
O2—C1	1.429 (5)	C5—H5B	0.9600
O3—C6	1.192 (6)	C5—H5C	0.9600
O4—C8	1.333 (6)	C6—C7	1.485 (7)
O4—C2	1.441 (5)	C7—H7A	0.9600
O5—C8	1.183 (6)	C7—H7B	0.9600
O6—C10	1.344 (4)	C7—H7C	0.9600
O6—C3	1.425 (5)	C8—C9	1.475 (6)
O7—C10	1.190 (5)	C9—H9A	0.9600
C1—C2	1.502 (6)	C9—H9B	0.9600
C1—H1	0.9800	C9—H9C	0.9600
C2—C3	1.500 (6)	C10—C11	1.484 (6)
C2—H2	0.9800	C11—H11A	0.9600
C3—C4	1.509 (5)	C11—H11B	0.9600
C3—H3	0.9800	C11—H11C	0.9600
C1—O1—C4	110.6 (3)	C4—C5—H5C	109.5
C6—O2—C1	117.4 (4)	H5A—C5—H5C	109.5
C8—O4—C2	116.5 (3)	H5B—C5—H5C	109.5
C10—O6—C3	116.6 (3)	O3—C6—O2	121.4 (5)
O1—C1—O2	110.4 (4)	O3—C6—C7	125.8 (5)
O1—C1—C2	107.5 (4)	O2—C6—C7	112.7 (5)
O2—C1—C2	106.3 (3)	C6—C7—H7A	109.5
O1—C1—H1	110.8	C6—C7—H7B	109.5
O2—C1—H1	110.8	H7A—C7—H7B	109.5
C2—C1—H1	110.8	C6—C7—H7C	109.5
O4—C2—C1	108.4 (3)	H7A—C7—H7C	109.5
O4—C2—C3	108.5 (4)	H7B—C7—H7C	109.5
C1—C2—C3	101.0 (4)	O5—C8—O4	121.9 (5)
O4—C2—H2	112.7	O5—C8—C9	126.3 (5)
C1—C2—H2	112.7	O4—C8—C9	111.8 (5)
C3—C2—H2	112.7	C8—C9—H9A	109.5
O6—C3—C2	116.1 (4)	C8—C9—H9B	109.5
O6—C3—C4	109.5 (3)	H9A—C9—H9B	109.5
C2—C3—C4	104.0 (3)	C8—C9—H9C	109.5
O6—C3—H3	109.0	H9A—C9—H9C	109.5
C2—C3—H3	109.0	H9B—C9—H9C	109.5
C4—C3—H3	109.0	O7—C10—O6	122.6 (4)
O1—C4—C5	109.4 (4)	O7—C10—C11	126.1 (4)
O1—C4—C3	104.1 (3)	O6—C10—C11	111.4 (4)
C5—C4—C3	115.6 (4)	C10—C11—H11A	109.5
O1—C4—H4	109.1	C10—C11—H11B	109.5
C5—C4—H4	109.1	H11A—C11—H11B	109.5
C3—C4—H4	109.1	C10—C11—H11C	109.5
C4—C5—H5A	109.5	H11A—C11—H11C	109.5
C4—C5—H5B	109.5	H11B—C11—H11C	109.5
H5A—C5—H5B	109.5