TY - JOUR
T1 - Three closely related dibenzazepine carboxylic acids
T2 - hydrogen-bonded aggregation in one, two and three dimensions
AU - Sanabria, Carlos M.
AU - Palma, Alirio
AU - Cobo, Justo
AU - Glidewell, Christopher
N1 - The authors thank the Centro de Instrumentacio´n Cientı´- fico-Te´ cnica of the Universidad de Jae´n and the staff for the data collection. AP and CMS thank Colciencias for financial support (grant No. 1102-521-28229). JC thanks the Consejerı´a de Innovacio´ n, Ciencia y Empresa (Junta de Andalucı´a, Spain) and the Universidad de Jae´n for financial support.
PY - 2014/3
Y1 - 2014/3
N2 - 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.
AB - 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.
KW - crystal structure determination
KW - Dibenzo[b,e]azepine-6-carboxylic acid
KW - Hydrogen bonding
KW - Hydrogen-bonded supramolecular aggregation
KW - Keto acid
KW - Phenylphosphonic acid
KW - Mianserin
KW - Derivatives
KW - 4,4'-sulfonyldiphenol
KW - 4,4'-thiodiphenol
KW - Mirtazapine
KW - Antagonists
KW - Adducts
KW - Series
UR - http://onlinelibrary.wiley.com/doi/10.1107/S2053229614003568/suppinfo
U2 - 10.1107/S2053229614003568
DO - 10.1107/S2053229614003568
M3 - Article
SN - 0108-2701
VL - 70
SP - 332
EP - 337
JO - Acta Crystallographica Section C: Crystal Structure Communications
JF - Acta Crystallographica Section C: Crystal Structure Communications
IS - 3
ER -