Crystal structure and Hirshfeld surface analysis of 2-methyl-3-nitro-N-[(E)-(5-nitrothiophen-2-yl)methylidene]aniline

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Kansiz S., DEGE N., Öztürk S., AKDEMİR N., TARCAN E., Arslanhan A., ...More

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, vol.77, pp.138-145, 2021 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 77
  • Publication Date: 2021
  • Doi Number: 10.1107/s2056989021000529
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.138-145
  • Keywords: crystal structure, thiophene, 5-nitrothiophen-2-yl, Schiff base, Hirshfeld surface analysis, hydrogen bonding.
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The title compound, C12H9N3O4S, synthesized by condensation of 5-nitrothiophene-2-carbaldehyde and 2-methyl-3-nitroaniline, crystallizes in the orthorhombic space group P2(1)2(1)2(1). In the molecule, the aromatic benzene and thiophene rings are twisted with respect to each other, making a dihedral angle of 23.16 (7)degrees. In the crystal, molecules are linked by intermolecular C-H center dot center dot center dot O hydrogen bonds into chains extending along the c-axis direction. Weak pi-pi stacking interactions along the a-axis direction provide additional stabilization of the crystal structure. The roles of the various intermolecular interactions were clarified by Hirshfeld surface analysis, which reveals that the crystal packing is dominated by O center dot center dot center dot H (39%) and H center dot center dot center dot H (21.3%) contacts. The crystal studied was refined as a two-component inversion twin.