Crystal structure and Hirshfeld surface analysis of two 5,11-methano­benzo[g][1,2,4]triazolo[1,5-c][1,3,5]oxa­diazo­cine derivatives

In the title compounds, 9-bromo-2,5-dimethyl-11,12-di­hydro-5H-5,11-methano­benzo[g][1,2,4]triazolo[1,5-c][1,3,5]oxa­diazo­cine, C(13)H(13)BrN(4)O (I), and 7-meth­oxy-5-methyl-2-(pyridin-4-yl)-11,12-di­hydro-5H-5,11-methano­benzo[g][1,2,4]tri­azolo[1,5-c][1,3,5]oxa­diazo­cine, C(18)H(17)N(5)O(2) (II), the triazole ring is inclined to the benzene ring by 85.15 (9) and 76.98 (5)° in compounds I and II, respectively. In II, the pyridine ring is almost coplanar with the triazole ring, having a dihedral angle of 4.19 (8)°. In the crystal of I, pairs of N—H⋯N hydrogen bonds link the mol­ecules to form inversion dimers with an R (2) (2)(8) ring motif. The dimers are linked by C—H⋯π and C—Br⋯π inter­actions forming layers parallel to the bc plane. In the crystal of II, mol­ecules are linked by N—H⋯N and C—H⋯O hydrogen bonds forming chains propagating along the b-axis direction. The inter­molecular inter­actions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the mol­ecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of I suggests that the most significant contributions to the crystal packing are H⋯H (42.4%) and O⋯H/H⋯O (17.9%) contacts. For compound II, the H⋯H (48.5%), C⋯H/H⋯C (19.6%) and N⋯H/H⋯N (16.9%) inter­actions are the most important contributions.