5-Fluoro-1-[(4S,5R)-5-(2-hydroxy­ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrimidine-2,4(1H,3H)-dione

Mendoza, A.; Sosa-Rivadeneyra, M.; Sartillo-Piscil, F.; Quintero, L.; Flores-Alamo, M.

doi:10.1107/S1600536810016065

Volume 66
Part 6
Page o1317
June 2010

Received 26 April 2010
Accepted 30 April 2010
Online 12 May 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.027
wR = 0.071
Data-to-parameter ratio = 9.9
Details

5-Fluoro-1-[(4S,5R)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrimidine-2,4(1H,3H)-dione

Angel Mendoza,^a ^* Martha Sosa-Rivadeneyra,^b Fernando Sartillo-Piscil,^b Leticia Quintero ^b and Marcos Flores-Alamo ^c

^aCentro de Química, ICUAP, Benemérita Universidad Autónoma de Puebla, Puebla, Pue., Mexico,^bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla, Pue., Mexico, and ^cFacultad de Química, Universidad Nacional Autónoma de México, 04510, México, DF, Mexico
Correspondence e-mail: angel.mendoza.m@gmail.com

In the title compound, C₁₁H₁₅FN₂O₅, the five-membered ring has an envelope conformation, while the six-membered ring is essentially planar, with a maximum deviation of 0.032 (2) Å from the mean plane. The crystal packing is stabilized by intermolecular N-HO and O-HO hydrogen bonds, generating a layer structure parallel to (001).

Related literature

For applications of modified nucleosides in medical chemistry, see: Huryn & Okabe (1992); Minuk et al. (1992); Luscombe et al. (1996); Korba & Boyd (1996). For the synthesis, see: Valdivia et al. (2005); Xie et al. (1996). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₁H₁₅FN₂O₅
M_r = 274.25
Monoclinic, C 2
a = 20.8905 (8) Å
b = 5.5751 (1) Å
c = 13.5639 (5) Å
= 126.297 (6)°
V = 1273.21 (12) Å³
Z = 4
Cu K radiation
= 1.06 mm^-1
T = 298 K
0.40 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Gemini Atlas CCD diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.885, T_max = 0.964
4606 measured reflections
1786 independent reflections
1732 reflections with I > 2(I)
R_int = 0.013

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.071
S = 1.04
1786 reflections
181 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.20 e Å^-3
Absolute structure: Flack (1983), 498 Friedel pairs
Flack parameter: 0.0 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H1NO5ⁱ	0.83 (2)	2.01 (2)	2.828 (2)	167 (3)
O5-H1OO2ⁱⁱ	0.75 (3)	2.16 (3)	2.876 (2)	160 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2543 ).

Acknowledgements

Special thanks to BUAP for financial support.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Huryn, D. M. & Okabe, M. (1992). Chem. Rev. 92, 1745-1768.
Korba, B. E. & Boyd, M. R. (1996). Antimicrob. Agents Chemother. 40, 1282-1284.
Luscombe, C., Pedersen, J., Uren, E. & Locarnini, S. (1996). Hepatology 24, 766-773.
Minuk, G. Y., German, G. B., Bernstein, C., Benarroch, A., Gauthiar, T. & Sekla, L. (1992). Clin. Invest. Med. 15, 506-512.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Valdivia, V., Hernández, A., Rivera, A., Sartillo-Piscil, F., Loukaci, A., Fourrey, J.-L. & Quintero, L. (2005). Tetrahedron Lett. 46, 6511-6514.
Xie, M., Berges, D. A. & Robins, M. (1996). J. Org. Chem. 61, 5178-5179.

organic compounds