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Eight new crystal structures of 5‐(hydroxymethyl)uracil, 5‐carboxyuracil and 5‐carboxy‐2‐thiouracil: insights into the hydrogen‐bonded networks and the predominant conformations of the C5‐bound residues
Author(s) -
Seiler Vanessa Kristina,
Hützler Wilhelm Maximilian,
Bolte Michael
Publication year - 2016
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229616004861
Subject(s) - chemistry , uracil , hydrogen bond , intramolecular force , thiouracil , hydroxymethyl , stereochemistry , crystal structure , dimethyl sulfoxide , crystallography , molecule , medicinal chemistry , organic chemistry , medicine , dna , biochemistry , thyroid
In order to examine the preferred hydrogen‐bonding pattern of various uracil derivatives, namely 5‐(hydroxymethyl)uracil, 5‐carboxyuracil and 5‐carboxy‐2‐thiouracil, and for a conformational study, crystallization experiments yielded eight different structures: 5‐(hydroxymethyl)uracil, C 5 H 6 N 2 O 3 , (I), 5‐carboxyuracil– N , N ‐dimethylformamide (1/1), C 5 H 4 N 2 O 4 ·C 3 H 7 NO, (II), 5‐carboxyuracil–dimethyl sulfoxide (1/1), C 5 H 4 N 2 O 4 ·C 2 H 6 OS, (III), 5‐carboxyuracil– N , N ‐dimethylacetamide (1/1), C 5 H 4 N 2 O 4 ·C 4 H 9 NO, (IV), 5‐carboxy‐2‐thiouracil– N , N ‐dimethylformamide (1/1), C 5 H 4 N 2 O 3 S·C 3 H 7 NO, (V), 5‐carboxy‐2‐thiouracil–dimethyl sulfoxide (1/1), C 5 H 4 N 2 O 3 S·C 2 H 6 OS, (VI), 5‐carboxy‐2‐thiouracil–1,4‐dioxane (2/3), 2C 5 H 4 N 2 O 3 S·3C 6 H 12 O 3 , (VII), and 5‐carboxy‐2‐thiouracil, C 10 H 8 N 4 O 6 S 2 , (VIII). While the six solvated structures, i.e. (II)–(VII), contain intramolecular S (6) O—H…O hydrogen‐bond motifs between the carboxy and carbonyl groups, the usually favoured R 2 2 (8) pattern between two carboxy groups is formed in the solvent‐free structure, i.e. (VIII). Further R 2 2 (8) hydrogen‐bond motifs involving either two N—H…O or two N—H…S hydrogen bonds were observed in three crystal structures, namely (I), (IV) and (VIII). In all eight structures, the residue at the ring 5‐position shows a coplanar arrangement with respect to the pyrimidine ring which is in agreement with a search of the Cambridge Structural Database for six‐membered cyclic compounds containing a carboxy group. The search confirmed that coplanarity between the carboxy group and the cyclic residue is strongly favoured.