Different hydrogen-bonding modes in two closely related oximes
Authors:
- Grzegorz Edward Dutkiewicz,
- H.S. Yathirajan,
- R. Ramachandran,
- S. Kabilan,
- Maciej Kubicki
Abstract
Two closely related oximes, namely 1-chloro-acetyl-3-ethyl-2,6-diphenyl- piperidin-4-one oxime, C21H23ClN2O2, (I), and 1-chloro-acetyl-2,6-diphenyl-3-(propan-2-yl)piperidin-4-one oxime, C22H25ClN2O2, (II), despite their identical sets of hydrogen-bond donors and acceptors, display basically different hydrogen-bonding patterns in their crystal structures. While the mol-ecules of (I) are organized into typical centrosymmetric dimers, created by oxime-oxime O-H⋯N hydrogen bonds, in the structure of (II) there are infinite chains of mol-ecules connected by O-H⋯O hydrogen bonds, in which the carbonyl O atom from the chloro-acetyl group acts as the hydrogen-bond acceptor. Despite the differences in the hydrogen-bond schemes, the-OH groups are always in typical anti positions (C-N-O-H torsion angles of ca 180°). The oxime group in (I) is disordered, with the hydroxy groups occupying two distinct positions and C-C-N-O torsion angles of approximately 0 and 180° for the two alternatives. This disorder, even though the site-occupancy factor of the less occupied position is as low as ca 0.06, is also observed at lower temperatures, which seems to favour the statistical and not the dynamic nature of this phenomenon. © 2010 International Union of Crystallography.
- Record ID
- UAM8368b770b3ba46bb87b6a5077e8a96b0
- Author
- Journal series
- Acta Crystallographica Section C-Crystal Structure Communications, ISSN 0108-2701
- Issue year
- 2010
- Vol
- 66
- ASJC Classification
- ;
- DOI
- DOI:10.1107/S0108270110015532 Opening in a new tab
- Language
- (en) English
- Score (nominal)
- 0
- Score source
- journalList
- Publication indicators
- = 1; = 1; : 2010 = 0.396; : 2010 (2 years) = 0.745 - 2010 (5 years) =0.630
- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAM8368b770b3ba46bb87b6a5077e8a96b0/
- URN
urn:amu-prod:UAM8368b770b3ba46bb87b6a5077e8a96b0
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.