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.

pdfdisplay filedownload file

Portable Document Format (PDF) file
[ doi:10.1107/S2053229614001387/eg3147sup10.pdf ]
Packing diagram for (I) showing the tubular arrangement of the chains


To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster