Crystal structure of the 1,3,6,8-tetra­aza­tri­cyclo[,8]undecane (TATU)–4-nitro­phenol (1/2) adduct : the role of anomeric effect in the formation of a second hydrogen-bond inter­action

  • In the title ternary co-crystalline adduct, C7H14N4·2C6H5NO3, mol­ecules are linked by two inter­molecular O—H⋯N hydrogen bonds, forming a tricomponent aggregates in the asymmetric unit. The hydrogen-bond formation to one of the N atoms is enough to induce structural stereoelectronic effects in the normal donor→acceptor direction. In the title adduct, the two independent nitro­phenol mol­ecules are essentially planar, with maximum deviations of 0.0157 (13) and 0.0039 (13) Å. The dihedral angles between the planes of the nitro group and the attached benzene rings are 4.04 (17) and 5.79 (17)°. In the crystal, aggregates are connected by C—H⋯O hydrogen bonds, forming a supra­molecular dimer enclosing an R66(32) ring motif. Additional C—H⋯O inter­molecular hydrogen-bonding inter­actions form a second supra­molecular inversion dimer with an R22(10) motif. These units are linked via C—H⋯O and C—H⋯N hydrogen bonds, forming a three-dimensional network.

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Author:Augusto RiveraORCiD, Héctor Jairo OsorioORCiD, Juan Manuel Uribe, Jaime Ríos-MottaORCiD, Michael BolteORCiD
Parent Title (German):Acta crystallographica. Section E, Crystallographic communications, 71.2015, S. 1356-1360
Publisher:International Union of Crystallography
Place of publication:Chester
Document Type:Article
Year of Completion:2015
Year of first Publication:2015
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2016/01/29
Tag:cocrystalline adducts; crystal structure; hydrogen bonding
Page Number:11
First Page:1356
Last Page:1360
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.
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - Namensnennung 2.0