Date Published: August 01, 2009
Publisher: International Union of Crystallography
Author(s): Qi-Hua Zhao, Li-Nan Li, Kun-Miao Wang.
In the title compound, C11H10ClN3S, the dihedral angle between the benzene and pyrimidine rings is 3.99 (4)°. In the crystal, intermolecular N—H⋯N hydrogen bonds link the molecules into ribbons of R22(8) rings parallel to . Weak C—H⋯S contacts connect adjacent ribbons into a two-dimensional undulating layer-like structure extending parallel to (110). The benzene and pyrimidine rings of adjacent molecules have the offset face-to-face π–π stacking interactions in a zigzag fashion along the c axis, with perpendicular ring distances of 3.463 and 3.639 Å, and a dihedral angle between the planes of 3.99 (2)°. The distance between the ring centroids is 4.420 (2) Å.
For the synthesis of pyrimidine-5-carbaldehydes from α-formylaroylketene dithioacetals, see: Mathews & Asokan (2007 ▶). For the synthesis of a 6-aryl aminopyrimidine compound, see: Lin et al. (2008 ▶). For the application of organic compounds as ligands, see: Li et al. (2007 ▶). For the importance aminopyrimidine compounds in the synthesis of complexes, see: Cui & Lan (2007 ▶). For a review of intermolecular C—H⋯S contacts, see: Taylor & Kennard (1982 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).