Crystal structure and Hirshfeld surface analysis of 5-[(5-nitro-1H-indazol-1-yl)methyl]-3-phenyl-4,5-dihydroisoxazole

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Boulhaoua M., Kansiz S., El Hafi M., Lahmidi S., DEGE N., Benchidmi M., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.75, pp.71-79, 2019 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 75
  • Publication Date: 2019
  • Doi Number: 10.1107/s2056989018017590
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.71-79
  • Keywords: crystal structure, indazole, oxazole, hydrogen bond, pi-pi-stacking, Hirshield surface analysis, BIOLOGICAL EVALUATION, DERIVATIVES
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

In the title compound, C17H14N4O3, the indazole unit is planar to within 0.0171 (10) angstrom and makes dihedral angles of 6.50 (6) and 6.79 (4)degrees, respectively, with the nitro and pendant phenyl groups. The conformation of the oxazole ring is best described as an envelope. In the crystal, oblique stacks along the a-axis direction are formed by pi-pi stacking interactions between the indazole unit and the pendant phenyl rings of adjacent molecules. The stacks are linked into pairs through C-H center dot center dot center dot O hydrogen bonds. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H center dot center dot center dot H (36.3%), O center dot center dot center dot H/H center dot center dot center dot O (23.4%), C center dot center dot center dot H/H center dot center dot center dot C (13.4%) and N center dot center dot center dot H/H center dot center dot center dot N (11.4%) interactions.