Syntheses and crystal structure of 4-[(pyridin-3-yl)diazen­yl]morpholine and 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline

Two new heterocyclic 1,2,3-triazenes were synthesized by diazo­tation of 3-amino­pyridine following respectively by coupling with morpholine or 1,2,3,4-tetra­hydro­quinoline. 4-[(Pyridin-3-yl)diazen­yl]morpholine (I), C(9)H(12)N(4)O, has monoclinic P2(1)/c symmetry at 100 K, while 1-[(pyridin-3-yl)diazen­yl]-1,2,3,4-tetra­hydro­quinoline (II), C(14)H(14)N(4), has monoclinic P2(1)/n symmetry at 100 K. These 1,2,3-triazene derivatives were synthesized by the organic medium method by coupling reactions of 3-amino­pyridine with morpholine and 1,2,3,4-tetra­hydro­quinoline, respectively, and characterized by (1)H NMR, (13)C NMR, IR, mass spectrometry, and single-crystal X-ray diffraction. The mol­ecule of compound I consists of pyridine and morpholine rings connected by an azo moiety (–N=N–). In the mol­ecule of II, the pyridine ring and the 1,2,3,4-tetra­hydro­quinoline unit are also connected by an azo moiety. The double- and single-bond distances in the triazene chain are comparable for the two compounds. In both crystal structures, the mol­ecules are connected by C—H⋯N inter­actions, forming infinite chains for I and layers parallel to the bc plane for II.