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

Carlos M. Sanabria; Alirio Palma; Justo Cobo; Christopher Glidewell

doi:10.1107/S2053229614003568

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

School of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	332-337
Number of pages	21
Journal	Acta Crystallographica Section C: Crystal Structure Communications
Volume	70
Issue number	3
DOIs	https://doi.org/10.1107/S2053229614003568
Publication status	Published - 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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Glidewell_2014_OC_Three
Copyright 2014 International Union of Crystallography
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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 R22(8) dimer motif characteristic of simple carboxylic acids.",

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",

author = "Sanabria, \{Carlos M.\} and Alirio Palma and Justo Cobo and Christopher Glidewell",

note = "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.",

year = "2014",

month = mar,

doi = "10.1107/S2053229614003568",

language = "English",

volume = "70",

pages = "332--337",

journal = "Acta Crystallographica Section C: Crystal Structure Communications",

issn = "0108-2701",

publisher = "International Union of Crystallography",

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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

UR - https://www.scopus.com/pages/publications/84904857757

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 -

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

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Keywords

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