Cocrystals of 6-methyl-2-thiouracil: presence of the acceptor-donor-acceptor/donor-acceptor-donor synthon

Acta Crystallographica. Section C, Structural Chemistry
Wilhelm Maximilian Hützler, Ernst Egert

Abstract

The results of seven cocrystallization experiments of the antithyroid drug 6-methyl-2-thiouracil (MTU), C(5)H(6)N(2)OS, with 2,4-diaminopyrimidine, 2,4,6-triaminopyrimidine and 6-amino-3H-isocytosine (viz. 2,6-diamino-3H-pyrimidin-4-one) are reported. MTU features an ADA (A = acceptor and D = donor) hydrogen-bonding site, while the three coformers show complementary DAD hydrogen-bonding sites and therefore should be capable of forming an ADA/DAD N-H...O/N-H...N/N-H...S synthon with MTU. The experiments yielded one cocrystal and six cocrystal solvates, namely 6-methyl-2-thiouracil-2,4-diaminopyrimidine-1-methylpyrrolidin-2-one (1/1/2), C(5)H(6)N(2)OS·C(4)H(6)N(4)·2C(5)H(9)NO, (I), 6-methyl-2-thiouracil-2,4-diaminopyrimidine (1/1), C(5)H(6)N(2)OS·C(4)H(6)N(4), (II), 6-methyl-2-thiouracil-2,4-diaminopyrimidine-N,N-dimethylacetamide (2/1/2), 2C(5)H(6)N(2)OS·C(4)H(6)N(4)·2C(4)H(9)NO, (III), 6-methyl-2-thiouracil-2,4-diaminopyrimidine-N,N-dimethylformamide (2/1/2), C(5)H(6)N(2)OS·0.5C(4)H(6)N(4)·C(3)H(7)NO, (IV), 2,4,6-triaminopyrimidinium 6-methyl-2-thiouracilate-6-methyl-2-thiouracil-N,N-dimethylformamide (1/1/2), C(4)H(8)N(5)(+)·C(5)H(5)N(2)OS(-)·C(5)H(6)N(2)OS·2C(3)H(7)NO, (V), 6-methyl-2-thiouracil-6-amino-3H-isocytosine-N,N-dim...Continue Reading

References

Jul 10, 2001·Angewandte Chemie·Leonard J. PrinsPeter Timmerman
Jul 1, 1962·Endocrinology·J M HERSHMAN, L VAN MIDDLESWORTH
Sep 29, 2007·Angewandte Chemie·Gautam R Desiraju
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
May 13, 2008·Drug Discovery Today·Ning Shan, Michael J Zaworotko
Jun 9, 2009·Crystal Growth & Design·Nate Schultheiss, Ann Newman
Jan 3, 2014·Angewandte Chemie·Colin R Groom, Frank H Allen
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick

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Citations

Apr 2, 2015·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Valeska Gerhardt, Ernst Egert
Aug 4, 2016·Acta Crystallographica. Section C, Structural Chemistry·Wilhelm Maximilian HützlerMichael Bolte
Jan 6, 2018·Acta Crystallographica. Section C, Structural Chemistry·Wilhelm Maximilian Hützler, Michael Bolte
Jun 6, 2020·Acta Crystallographica. Section C, Structural Chemistry·Yong Jin ZhaoYu Bin Dong
Mar 4, 2017·Acta Crystallographica. Section C, Structural Chemistry·Xue Ru WangYu Bin Dong

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