Role of pK ain establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- And nitro-substituted benzoic acids

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Abstract

The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C10H10N+·C7H3ClNO4-, (I), 4-methylquinoline-2-chloro-5-nitrobenzoic acid (1/1), C10H9N·C7H4ClNO4, (II), 4-methylquinolinium 2-chloro-6-nitrobenzoate, C10H9.63N0.63+·C7H3.37ClNO40.63-, (III), 4-methylquinolinium 3-chloro-2-nitrobenzoate, C10H9.54N0.54+·C7H3.46ClNO40.54-, (IV), 4-methylquinolinium 4-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4-, (V), and 4-methylquinolinium 5-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4-, have been determined at 185-190 K. In each compound, the acid and base molecules are linked by a short hydrogen bond between a carboxy (or carboxylate) O atom and an N atom of the base. The O...N distances are 2.5652 (14), 2.556 (3), 2.5485 (13), 2.5364 (13), 2.5568 (13) and 2.5252 (11) Å, respectively, for compounds (I)-(VI). In the hydrogen-bonded acid-base units of (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.37 (3):0.63 (3) and 0.46 (3):0.54 (4), respectively, for (III) and (IV). The H atoms in the hydrogen-bonded units of (I), (V) and (VI) are located at the N-atom site, while the H atom in (II) is located at the O-atom site. In all the crystals of (I)-(VI), π-π stacking interactions between the quinoline ring systems and C - H...O hydrogen bonds are observed. Similar layer structures are constructed in (IV)-(VI) through these interactions together with π-π interactions between the benzene rings of the adjacent acid molecules. A short Cl...Cl contact and an N - O...π interaction are present in (I), while a C - H...Cl hydrogen bond and a π-π interaction between the benzene ring of the acid molecule and the quinoline ring system in (II), and a C - H...π interaction in (III) are observed. Hirshfeld surfaces for the title compounds mapped over d norm and shape index were generated to visualize the weak intermolecular interactions.

Original languageEnglish
Pages (from-to)1144-1152
Number of pages9
JournalActa Crystallographica Section E: Crystallographic Communications
Volume77
DOIs
Publication statusPublished - Nov 1 2021

Keywords

  • 2-chloro-4-nitrobenzoic acid
  • 2-chloro-5-nitrobenzoic acid
  • 2-chloro-6-nitrobenzoic acid
  • 3-chloro-2-nitrobenzoic acid
  • 4-chloro-2-nitrobenzoic acid
  • 4-methylquinoline
  • 5-chloro-2-nitrobenzoic acid
  • Crystal structure
  • Disorder
  • Hirshfeld surface
  • Hydrogen bond

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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