Crystal structure and Hirshfeld surface analysis of two 5,11-methanobenzo[g][1,2,4]triazolo[1,5 c][1,3,5]oxadiazocine derivatives
Citation
Gümüş, M. K., Kansız, S., Yüksektepe Ataol, C., Dege, N., & Fritsky, I. O. (2019). Crystal structure and Hirshfeld surface analysis of two 5, 11-methanobenzo [g][1, 2, 4] triazolo [1, 5-c][1, 3, 5] oxadiazocine derivatives. Acta Crystallographica Section E: Crystallographic Communications, 75, 492-498. Doi: 10.1107/S2056989019003700Abstract
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, C13H13BrN4O (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, C18H17N5O2 (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—HN hydrogen bonds link the
molecules to form inversion dimers with an R2
2
(8) ring motif. The dimers are
linked by C—H and C—Br interactions forming layers parallel to the bc
plane. In the crystal of II, molecules are linked by N—HN and C—HO
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 HH (42.4%) and
OH/HO (17.9%) contacts. For compound II, the HH (48.5%), CH/
HC (19.6%) and NH/HN (16.9%) interactions are the most important
contributions.