Synthesis and crystal structure of ebastinium hydrogen fumarate

Prabhakar Priyanka, Bidarur K. Jayanna, Haruvegowda Kiran Kumar, Vinaya, Thayamma R. Divakara, Hemmige S. Yathirajan, Sean Parkin, W. T.A. Harrison

Research output: Contribution to journalArticlepeer-review

Abstract

The structure of ebastinium hydrogen fumarate {systematic name: 1-[4-(4-tert-butylphenyl)-4-oxobutyl]-4-(diphenylmethoxy)piperidin-1-ium (E)-3-carboxy-1-hydroxyprop-2-en-1-olate}, C32H40NO2 +·C4H3O4 -, a 1:1 salt formed in the reaction between ebastine and fumaric acid is presented. All examined crystals were found to be twinned by pseudo-merohedry. The structure is extensively disordered, with over half (20 out of 35) its non-hydrogen atoms modelled as lying over two sets of sites. In the crystal, cation-anion pairs are linked by a strong N-HO hydrogen bond [NO = 2.697 (11) Å]. These units interact via weaker C-HO and C-Hπ contacts to form layers lying parallel to the bc plane. The hydrogen fumarate anions are linked by a very short O-HO hydrogen bond [OO = 2.5402 (17) Å], augmented by weak C-HO contacts into pairs of R 2 2(6) ring motifs to form chains that extend parallel to the b-axis direction. Comparisons to similar crystal structures are presented.

Original languageEnglish
Pages (from-to)916-921
Number of pages6
JournalActa Crystallographica Section E: Crystallographic Communications
Volume78
DOIs
StatePublished - Sep 1 2022

Bibliographical note

Funding Information:
PP thanks the B. N. M. Institute of Technology, Bangalore, India for research facilities. The D8 Venture diffractometer was funded by the NSF (MRI CHE1625732), and by the University of Kentucky.

Publisher Copyright:
© 2022 Priyanka et al.

Keywords

  • crystal structure
  • disorder
  • ebastine
  • hydrogen fumarate
  • pseudo-merohedral twinning

ASJC Scopus subject areas

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

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