Crystal structure of 2-(azaniumylmethyl)pyridinium bis(hydrogen squarate)

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Salamzadeh N., Demircioglu Z., Korkmaz U., Buyukgungor O.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.73, pp.586-594, 2017 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 73
  • Publication Date: 2017
  • Doi Number: 10.1107/s2056989017004376
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.586-594
  • Keywords: crystal structure, 2-(azaniumylmethyl)pyridinium, squaric acid, hydrogen bonding, SQUARIC ACID, HYDROGEN SQUARATE, DENSITY, ANIONS
  • Ondokuz Mayıs University Affiliated: Yes

Abstract

The asymmetric unit of the title compound, C6H10N22+center dot 2C(4)HO(4)(-), comprises two hydrogen squarate (Hsq(-); systematic name: 2-hydroxy-3,4-dioxocyclobutanolate) anions and a 2-(azaniumylmethyl) pyridinium dication. The squaric acid molecules each donate an H atom to the N atoms of the pyridine ring and the aminomethyl units of a 2-(aminomethyl) pyridine molecule, forming the 1: 2 salt. The Hsq(-) anions are linked by strong O-H center dot center dot center dot O hydrogen bonds and an N-H center dot center dot center dot O hydrogen bond links the 2-(azaniumylmethyl) pyridinium cation to one of the squaric acid anions. The crystal structure features additional N-H center dot center dot center dot O and O-H center dot center dot center dot O hydrogen bonds, pi-pi stacking and unusual weak C-O center dot center dot center dot pi (ring) interactions.