• Title of article

    Crystal structure of 4-chloro-2-nitro­benzoic acid with 4-hy­dr­oxy­quinoline: a disordered structure over two states of 4-chloro-2-nitro­benzoic acid–quinolin-4(1H)-one (1/1) and 4-hy­dr­oxy­quinolinium 4-chloro-2-nitro­benzoate

  • Author/Authors

    Gotoh, Kazuma Department of Chemistry - Faculty of Science - Okayama University, Japan , Ishida, Hiroyuki Department of Chemistry - Faculty of Science - Okayama University, Japan

  • Pages
    9
  • From page
    1
  • To page
    9
  • Abstract
    The title compound, C9H7.5NO·C7H3.5ClNO4, was analysed as a disordered structure over two states, viz. co-crystal and salt, accompanied by a keto–enol tautomerization in the base mol­ecule. The co-crystal is 4-chloro-2-nitro­benzoic acid–quinolin-4(1H)-one (1/1), C7H4ClNO4·C9H7NO, and the salt is 4-hy­droxy­quinolinium 4-chloro-2-nitro­benzoate, C9H8NO+·C7H3ClNO4−. In the compound, the acid and base mol­ecules are held together by a short hydrogen bond [O⋯O = 2.4393 (15) Å], in which the H atom is disordered over two positions with equal occupancies. In the crystal, the hydrogen-bonded acid–base units are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming a tape structure along the a-axis direction. The tapes are stacked into a layer parallel to the ab plane via π–π inter­actions [centroid–centroid distances = 3.5504 (8)–3.9010 (11) Å]. The layers are further linked by another C—H⋯O hydrogen bond, forming a three-dimensional network. Hirshfeld surfaces for the title compound mapped over shape-index and dnorm were generated to visualize the inter­molecular inter­actions.
  • Keywords
    crystal structure , 4(1H)-quinolinone , 4-hy­droxy­quinoline , hydrogen bond , keto–enol tautomerization
  • Journal title
    Acta Crystallographica Section E: Crystallographic Communications
  • Serial Year
    2019
  • Record number

    2624591