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

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GÜMÜŞ M. K., Kansiz S., YÜKSEKTEPE ATAOL Ç., DEGE N., Fritsky I. O.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, cilt.75, ss.492-507, 2019 (ESCI) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 75
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1107/s2056989019003700
  • Dergi Adı: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Sayfa Sayıları: ss.492-507
  • Anahtar Kelimeler: crystal structure, Biginelli condensation, benzoxadiazocine, hydrogen bonding, C-H center dot center dot center dot pi interactions, C-Br center dot center dot center dot pi interactions, Hirshfeld surface analysis, 3-AMINO-1,2,4-TRIAZOLE
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

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)degrees 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)degrees. In the crystal of I, pairs of N-H center dot center dot center dot 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 center dot center dot center dot pi and C-Br center dot center dot center dot pi interactions forming layers parallel to the bc plane. In the crystal of II, molecules are linked by N-H center dot center dot center dot N and C-H center dot center dot center dot 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 center dot center dot center dot H (42.4%) and O center dot center dot center dot H/H center dot center dot center dot O (17.9%) contacts. For compound II, the H center dot center dot center dot H (48.5%), C center dot center dot center dot H/H center dot center dot center dot C (19.6%) and N center dot center dot center dot H/H center dot center dot center dot N (16.9%) interactions are the most important contributions.