Research Article: 6-Chloro-N-(2-meth­oxy­phen­yl)pyridazin-3-amine

Date Published: February 01, 2012

Publisher: International Union of Crystallography

Author(s): Abdul Qayyum Ather, M. Nawaz Tahir, Muhammad Naeem Khan, Misbahul Ain Khan, Muhammad Makshoof Athar.


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.

Partial Text

For general background and related structures, see: Ather et al. (2010a ▶,b ▶,c ▶; 2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).