Research Article: 4-(4-Chloro­phen­yl)-6-(methyl­sulfan­yl)pyrimidin-2-amine

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 [100]. 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.

Partial Text

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 ▶).




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