title: Three closely related dibenzazepine carboxylic acids: hydrogen-bonded aggregation in one, two and three dimensions.
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 R2(2)(8) dimer motif characteristic of simple carboxylic acids.
authors.affiliation: Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678 Bucaramanga, Colombia.
authors.forename: Carlos M
authors.initials: CM
authors.lastname: Sanabría
authors.affiliation: Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, AA 678 Bucaramanga, Colombia.
authors.forename: Alirio
authors.initials: A
authors.lastname: Palma
authors.affiliation: Departamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain.
authors.forename: Justo
authors.initials: J
authors.lastname: Cobo
authors.affiliation: School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D001552:Benzazepines / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003984:Dibenzazepines / Q000737:chemistry*; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: C000589792:(6R,11R)-5-acetyl-11-ethyl-6,11-dihydro-5H-dibenzo(b,e)azepine-6-carboxylic acid; D001552:Benzazepines; D002264:Carboxylic Acids; D003984:Dibenzazepines; C527817:dibenzazepine
keywords: crystal structure; dibenzo[b,e]azepine-6-carboxylic acid; hydrogen bonding; hydrogen-bonded supramolecular aggregation