Acta Crystallographica Section C

Volume 65, Part 11 (November 2009)


organic compounds



sk3347 scheme

Acta Cryst. (2009). C65, o574-o578    [ doi:10.1107/S010827010903950X ]

New pseudopolymorphs of 5-fluorocytosine

M. Tutughamiarso, M. Bolte and E. Egert

Abstract: In order to better understand the interaction between the pharmaceutically active compound 5-fluorocytosine [4-amino-5-fluoropyrimidin-2(1H)-one] and its receptor, hydrogen-bonded complexes with structurally similar bonding patterns have been investigated. During the cocrystallization screening, three new pseudopolymorphs of 5-fluorocytosine were obtained, namely 5-fluorocytosine dimethyl sulfoxide solvate, C4H4FN3O·C2H6OS, (I), 5-fluorocytosine dimethylacetamide hemisolvate, C4H4FN3O·0.5C4H9NO, (II), and 5-fluorocytosine hemihydrate, C4H4FN3O·0.5H2O, (III). Similar hydrogen-bond patterns are observed in all three crystal structures. The 5-fluorocytosine molecules form ribbons with repeated R22(8) dimer interactions. These dimers are stabilized by N-H...N and N-H...O hydrogen bonds. The solvent molecules adopt similar positions with respect to 5-fluorocytosine. Depending on the hydrogen bonds formed by the solvent, the 5-fluorocytosine ribbons form layers or tubes. A database study was carried out to compare the hydrogen-bond pattern of compounds (I)-(III) with those of other (pseudo)polymorphs of 5-fluorocytosine.

Formula: C4H4FN3O·C2H6OS, C4H4FN3O·0.5C4H9NO and C4H4FN3O·0.5H2O


hkldisplay filedownload file

Structure factor file (CIF format) (93.7 kbytes)
[ doi:10.1107/S010827010903950X/sk3347Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (142.9 kbytes)
[ doi:10.1107/S010827010903950X/sk3347IIsup3.hkl ]
Contains datablock II


hkldisplay filedownload file

Structure factor file (CIF format) (105.3 kbytes)
[ doi:10.1107/S010827010903950X/sk3347IIIsup4.hkl ]
Contains datablock III


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