meso-4,4'-Dimethoxy-2,2'-{[(3aR,7aS)- 2,3,3a,4,5,6,7,7a-octahydro-1H-benzimidazole- 1,3-diyl]bis(methylene)}- diphenol
Result description
The title compound, C23H30N2O4, a di-Mannich base derived from 4-methoxyphenol and cis-1,2-diaminecyclohexane, has a perhydrobenzimidazolidine nucleus, in which the cyclohexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C?N?C?C torsion angles of -48.14 (15) and -14.57 (16)°. The mean plane of the heterocycle makes dihedral angles of 86.29 (6) and 78.92 (6) with the pendant benzene rings. The molecular structure of the title compound shows the presenceof two interactions between the N atoms of the imidazolidine ring and the hydroxyl groups through intramolecular O?H...N hydrogen bonds with graph-set motif S(6). The unobserved lone pairs of the N atoms are presumed to be disposed in a syn conformation, being only the second example of an exception to the typical rabbit-ears? effect in 1,2-diamines.
Keywords
single-crystal X-ray studyT = 120 Kmean sigma(C?C) = 0.003 AR factor = 0.031wR factor = 0.080data-to-parameter ratio = 13.0
The result's identifiers
Result code in IS VaVaI
Result on the web
DOI - Digital Object Identifier
Alternative languages
Result language
angličtina
Original language name
meso-4,4'-Dimethoxy-2,2'-{[(3aR,7aS)- 2,3,3a,4,5,6,7,7a-octahydro-1H-benzimidazole- 1,3-diyl]bis(methylene)}- diphenol
Original language description
The title compound, C23H30N2O4, a di-Mannich base derived from 4-methoxyphenol and cis-1,2-diaminecyclohexane, has a perhydrobenzimidazolidine nucleus, in which the cyclohexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C?N?C?C torsion angles of -48.14 (15) and -14.57 (16)°. The mean plane of the heterocycle makes dihedral angles of 86.29 (6) and 78.92 (6) with the pendant benzene rings. The molecular structure of the title compound shows the presenceof two interactions between the N atoms of the imidazolidine ring and the hydroxyl groups through intramolecular O?H...N hydrogen bonds with graph-set motif S(6). The unobserved lone pairs of the N atoms are presumed to be disposed in a syn conformation, being only the second example of an exception to the typical rabbit-ears? effect in 1,2-diamines.
Czech name
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Czech description
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Classification
Type
Jx - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
BM - Solid-state physics and magnetism
OECD FORD branch
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Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2013
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Acta Crystallographica section E - Structure Reports Online
ISSN
1600-5368
e-ISSN
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Volume of the periodical
69
Issue of the periodical within the volume
7
Country of publishing house
DK - DENMARK
Number of pages
2
Pages from-to
"o1057"-"o1058"
UT code for WoS article
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EID of the result in the Scopus database
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Basic information
Result type
Jx - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP
BM - Solid-state physics and magnetism
Year of implementation
2013