5-O-Acetyl-d-ribono-1,4-lactone

Bortoluzzi, A.J.; Sebrão, D.; Sá, M.M.; Nascimento, M.G.

doi:10.1107/S1600536811038670

Volume 67
Part 10
Page o2778
October 2011

Received 6 August 2011
Accepted 20 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 10.6
Details

5-O-Acetyl-D-ribono-1,4-lactone

Adailton J. Bortoluzzi,^a ^* Damianni Sebrão,^a Marcus M. Sá ^a and M. G. Nascimento ^a

^aDepto. de Química - UFSC, 88040-900 - Florianópolis, SC, Brazil
Correspondence e-mail: adajb@qmc.ufsc.br

The title compound, C₇H₁₀O₆, was obtained from a regioselective enzyme-catalysed acylation of D-ribono-1,4-lactone. The five-membered ring of the acylated sugar shows an envelope conformation. In the crystal, the molecules are linked by intermolecular O-HO hydrogen-bonds, forming a one-dimensional polymeric structure parallel to [010]. In addition, packing analysis shows stacking along the b axis.

Related literature

For general background to carbohydrates, see: Corma et al. (2007); Han et al. (1993); Simone et al. (2005). For biocatalysed acylation reactions, see: Díaz-Rodríguez et al. (2005); Wu et al. (2008). For related structures, see: Shalaby et al. (1994); Bye (1979); Amador et al. (2004); Sá et al. (2008); Gress & Jeffrey (1976).

Experimental

Crystal data

C₇H₁₀O₆
M_r = 190.15
Monoclinic, P 2₁
a = 6.1409 (4) Å
b = 5.1952 (15) Å
c = 13.1844 (18) Å
= 95.118 (12)°
V = 418.95 (14) Å³
Z = 2
Mo K radiation
= 0.13 mm^-1
T = 293 K
0.50 × 0.30 × 0.13 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
2164 measured reflections
1346 independent reflections
1015 reflections with I > 2(I)
R_int = 0.046
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.135
S = 1.07
1346 reflections
127 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.29 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3O4ⁱ	0.85 (5)	1.95 (5)	2.781 (3)	164 (3)
O4-H4O2ⁱ	0.85 (5)	2.15 (5)	2.910 (3)	148 (5)
O4-H4O3ⁱ	0.85 (5)	2.41 (6)	3.086 (4)	136 (4)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 in CAD-4 Software; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2026 ).

Acknowledgements

The authors thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and the Financiadora de Estudos e Projetos (FINEP) for financial support.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Amador, P., Flores, H. & Bernès, S. (2004). Acta Cryst. E60, o904-o906.
Bye, E. (1979). Acta Chem. Scand. 33, 169-171.
Corma, A., Iborra, S. & Velty, A. (2007). Chem. Rev. 107, 2411-2502.
Díaz-Rodríguez, A., Fernández, S., Lavandera, I., Ferrero, M. & Gotor, V. (2005). Tetrahedron Lett. 46, 5835-5838.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Gress, M. E. & Jeffrey, G. A. (1976). Carbohydr. Res. 50, 159-168.
Han, S.-Y., Joullié, M. M., Petasis, N. A., Bigorra, J., Corbera, J., Font, J. & Ortuño, R. M. (1993). Tetrahedron 49, 349-362.
Sá, M. M., Silveira, G. P., Caro, M. S. B. & Ellena, J. (2008). J. Braz. Chem. Soc. 19, 18-23.
Shalaby, M. A., Fronczek, F. R. & Younathan, E. S. (1994). Carbohydr. Res. 264, 181-190.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Simone, M. I., Soengas, R., Newton, C. R., Watkin, D. J. & Fleet, G. W. J. (2005). Tetrahedron Lett. 46, 5761-5765.
Spek, A. L. (1996). HELENA. University of Utrecht, The Netherlands.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wu, Q., Xia, A. & Lin, X. (2008). J. Mol. Catal. B Enzym. 54, 76-82.

organic compounds