6-Chloro-N-(2-methoxyphenyl)pyridazin-3-amine

Abstract

The asymmetric unit of the title compound, C11H10ClN3O, contains two geometrically different molecules, A and B, in both of which the pyridazine rings are essentially planar with r.m.s. deviations of 0.0137 and 0.0056Å, respectively. In molecule A, the dihedral angle between the pyridazine and benzene rings is 6.5 (2)°, whereas in molecule B it is 27.93 (7)°. In molecule B, an intramolecular N—H...O hydrogen bond forms an S(5) ring motif. In both molecules, S(6) ring motifs are present due to non-classical C—H...N hydrogen bonds. The π–π interactions between the pyridazine rings of A molecules [3.4740 (13) Å] and B molecules [3.4786 (17) Å] have very similar centroid–centroid separations. π–π Interactions also occur between the benzene rings of B molecules with a centroid–centroid separation of 3.676 (2) Å and a slippage of 1.02 Å. In the crystal, the molecules are linked into chains extending along [010] by C—H...N and C—H...Cl interactions.