Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 2 (February 2014)


computational materials discovery



eg3147 scheme

Acta Cryst. (2014). C70, 241-249    [ doi:10.1107/S2053229614001387 ]

N-H...S and N-H...O hydrogen bonds: `pure' and `mixed' R22(8) patterns in the crystal structures of eight 2-thio­uracil derivatives

W. M. Hützler and E. Egert

Abstract: The preferred hydrogen-bonding patterns in the crystal structures of 5-propyl-2-thio­uracil, C7H10N2OS, (I), 5-meth­oxy-2-thio­uracil, C5H6N2O2S, (II), 5-meth­oxy-2-thio­uracil-N,N-di­methyl­acetamide (1/1), C5H6N2O2S·C4H9NO, (IIa), 5,6-dimethyl-2-thio­uracil, C6H8N2OS, (III), 5,6-dimethyl-2-thio­uracil-1-methyl­pyrrolidin-2-one (1/1), C6H8N2OS·C5H9NO, (IIIa), 5,6-dimethyl-2-thio­uracil-N,N-di­methyl­formamide (2/1), 2C6H8N2OS·C3H7NO, (IIIb), 5,6-dimethyl-2-thio­uracil-N,N-di­methyl­acetamide (2/1), 2C6H8N2OS·C4H9NO, (IIIc), and 5,6-dimethyl-2-thio­uracil-di­methyl ­sulfoxide (2/1), 2C6H8N2OS·C2H6OS, (IIId), were analysed. All eight structures contain R22(8) patterns. In (II), (IIa), (III) and (IIIa), they are formed by two N-H...S hydrogen bonds, and in (I) by alternating pairs of N-H...S and N-H...O hydrogen bonds. In contrast, the structures of (IIIb), (IIIc) and (IIId) contain `mixed' R22(8) patterns with one N-H...S and one N-H...O hydrogen bond, as well as R22(8) motifs with two N-H...O hydrogen bonds.

Formula: C7H10N2OS, C5H6N2O2S, C5H6N2O2S·C4H9NO, C6H8N2OS, C6H8N2OS·C5H9NO, 2C6H8N2OS·C3H7NO, 2C6H8N2OS·C4H9NO and 2C6H8N2OS·C2H6OS

Keywords: crystal structure; mixed R22(8) patterns; N-H...S hydrogen bonds; N-H...O hydrogen bonds; 2-thio­uracil derivatives; active pharmaceutical ingredients.


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Structure factor file (CIF format) (155.2 kbytes)
[ doi:10.1107/S2053229614001387/eg3147Isup2.hkl ]
Contains datablock I


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Structure factor file (CIF format) (60.7 kbytes)
[ doi:10.1107/S2053229614001387/eg3147IIsup3.hkl ]
Contains datablock II


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Structure factor file (CIF format) (121.4 kbytes)
[ doi:10.1107/S2053229614001387/eg3147IIasup4.hkl ]
Contains datablock IIa


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Structure factor file (CIF format) (63.5 kbytes)
[ doi:10.1107/S2053229614001387/eg3147IIIsup5.hkl ]
Contains datablock III


hkldisplay filedownload file

Structure factor file (CIF format) (114.1 kbytes)
[ doi:10.1107/S2053229614001387/eg3147IIIasup6.hkl ]
Contains datablock IIIa


hkldisplay filedownload file

Structure factor file (CIF format) (174.4 kbytes)
[ doi:10.1107/S2053229614001387/eg3147IIIbsup7.hkl ]
Contains datablock IIIb


hkldisplay filedownload file

Structure factor file (CIF format) (182.8 kbytes)
[ doi:10.1107/S2053229614001387/eg3147IIIcsup8.hkl ]
Contains datablock IIIc


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Structure factor file (CIF format) (172.5 kbytes)
[ doi:10.1107/S2053229614001387/eg3147IIIdsup9.hkl ]
Contains datablock IIId


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