TY  - JOUR
A1  - Rivera, Augusto
A1  - Nerio, Luz Stella
A1  - Bolte, Michael
T1  - Crystal structure of the di-Mannich base 4,4′-di­chloro-3,3′,5,5′-tetra­methyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol
T2  - Acta crystallographica. Section E, Crystallographic communications
N2  - The title compound, C21H26Cl2N2O2, was prepared in a solvent-free microwave-assisted synthesis, and crystallizes in the ortho­rhom­bic space group Pna21. The imidazolidine ring adopts an envelope conformation and its mean plane is almost perpendicular to the two pendant aromatic rings [dihedral angles = 84.61 (9) and 86.54 (9)°]. The mol­ecular structure shows the presence of two intra­molecular O—H⋯N hydrogen bonds between the phenolic hy­droxy groups and imidazolidine N atoms. The two 3-chloro-6-hy­droxy-2,4-di­methyl­benzyl groups are located in a cis orientation with respect to the imidazolidine fragment. As a result, the lone pairs of electrons on the N atoms are presumed to be disposed in a syn conformation. This is therefore the first example of an exception to the `rabbit-ears' effect in such 2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol derivatives.
KW  - crystal structure
KW  - imidazolidine
KW  - diMannich base
KW  - hydrogen bonding
KW  - syn conformation
Y1  - 2015
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/54304
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-543047
SN  - 2056-9890
N1  - This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
VL  - 71
IS  - 3
SP  - 312
EP  - 314
PB  - International Union of Crystallography ; National Center for Biotechnology Information, U.S. National Library of Medicine
CY  - Chester ; Bethesda, MD
ER  -