Three closely related dibenzazepine carboxylic acids: hydrogen-bonded aggregation in one, two and three dimensions

Carlos M. Sanabria, Alirio Palma, Justo Cobo, Christopher Glidewell*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)
1 Downloads (Pure)

Abstract

In the structure of (6R*,11R*)-5-acetyl-11-ethyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-carboxylic acid, C19H19NO3, (I), the molecules are linked into sheets by a combination of O-H...O and C-H...O hydrogen bonds; in the structure of the monomethyl analogue (6RS,11SR)-5-acetyl-11-ethyl-2-methyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-carboxylic acid, C20H21NO3, (II), the molecules are linked into simple C(7) chains by O-H...O hydrogen bonds; and in the structure of the dimethyl analogue (6RS,11SR)-5-acetyl-11-ethyl-1,3-dimethyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-carboxylic acid, C21H23NO3, (III), a combination of O-H...O, C-H...O and C-H...π(arene) hydrogen bonds links the molecules into a three-dimensional framework structure. None of these structures exhibits the R22(8) dimer motif characteristic of simple carboxylic acids.

Original languageEnglish
Pages (from-to)332-337
Number of pages21
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume70
Issue number3
DOIs
Publication statusPublished - Mar 2014

Keywords

  • crystal structure determination
  • Dibenzo[b,e]azepine-6-carboxylic acid
  • Hydrogen bonding
  • Hydrogen-bonded supramolecular aggregation
  • Keto acid
  • Phenylphosphonic acid
  • Mianserin
  • Derivatives
  • 4,4'-sulfonyldiphenol
  • 4,4'-thiodiphenol
  • Mirtazapine
  • Antagonists
  • Adducts
  • Series

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