Crystal structure of 6-chloro-5-isopropylpyrimidine-2,4(1H,3H)-dione

• Main Authors: Nadia G. Haress, Hazem A. Ghabbour, Ali A. El-Emam, C. S. Chidan Kumar, Hoong-Kun Fun
• Format: Article
• Language: English
• Published: International Union of Crystallography 2014-11-01
• Series: Acta Crystallographica Section E
• Subjects: crystal structure; pyrimidine-2,4-dione; hydrogen bonds; π–π interaction
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S1600536814021382

In the molecule of the title compound, C7H9ClN2O2, the conformation is determined by intramolecular C—H...O and C—H...Cl hydrogen bonds, which generate S(6) and S(5) ring motifs. The isopropyl group is almost perpendicular to the pyrimidine ring with torsion angles of −70.8 (3) and 56.0 (3)°. In the crystal, two inversion-related molecules are linked via a pair of N—H...O hydrogen bonds into R22(8) dimers; these dimers are connected into chains extending along the bc plane via an additional N—H...O hydrogen bond and weaker C—H...O hydrogen bonds. The crystal structure is further stabilized by a weak π–π interaction [3.6465 (10) Å] between adjacent pyrimidine-dione rings arranged in a head-to-tail fashion, producing a three-dimensional network.