Crystal structure of the di-Mannich base 4,4′-di­chloro-3,3′,5,5′-tetra­methyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol

Crystal structure of the di-Mannich base 4,4′-dichloro-3,3′,5,5′-tetramethyl-2,2′-[imidazolidine-1,3-diylbis(methylene)]diphenol

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.

Metadaten
Author:	Augusto Rivera ORCiD, Luz Stella Nerio, Michael Bolte ORCiD
URN:	urn:nbn:de:hebis:30:3-543047
DOI:	https://doi.org/10.1107/S2056989015002212
ISSN:	2056-9890
Pubmed Id:	https://pubmed.ncbi.nlm.nih.gov/25844196
Parent Title (English):	Acta crystallographica. Section E, Crystallographic communications
Publisher:	International Union of Crystallography ; National Center for Biotechnology Information, U.S. National Library of Medicine
Place of publication:	Chester ; Bethesda, MD
Contributor(s):	J. Simpson
Document Type:	Article
Language:	English
Year of Completion:	2015
Date of first Publication:	2015/02/25
Publishing Institution:	Universitätsbibliothek Johann Christian Senckenberg
Release Date:	2020/06/17
Tag:	crystal structure; diMannich base; hydrogen bonding; imidazolidine; syn conformation
Volume:	71
Issue:	3
Page Number:	9
First Page:	312
Last Page:	314
Note:	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.
HeBIS-PPN:	46683618X
Institutes:	Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:	5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Sammlungen:	Universitätspublikationen
Licence (German):	Creative Commons - Namensnennung 2.0