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Redetermination of 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]dodeca-ne.

ABSTRACT: The structure of the title compound, C8H16N4, which consists of four fused seven-membered rings, has been redetermined at 173 K. This redetermination corrects the orientation of two H atoms, which were located at unrealistic positions in the original room-temperature study [Murray-Rust (1974 ▶). J. Chem. Soc. Perkin Trans. 2, pp. 1136-1141]. The complete mol-ecule is generated by -42m symmetry, with one quarter of a mol-ecule [one N atom (site symmetry m), two C atoms (one with site symmetry m and the other with site symmetry 2) and two H atoms] in the asymmetric unit. No directional inter-actions beyond van der Waals contacts are apparent in the crystal structure.

SUBMITTER: Rivera A

PROVIDER: S-EPMC3998434 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Redetermination of 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]dodeca-ne.

Rivera Augusto A Ríos-Motta Jaime J Bolte Michael M

Acta crystallographica. Section E, Structure reports online 20140208 Pt 3

The structure of the title compound, C8H16N4, which consists of four fused seven-membered rings, has been redetermined at 173 K. This redetermination corrects the orientation of two H atoms, which were located at unrealistic positions in the original room-temperature study [Murray-Rust (1974 ▶). J. Chem. Soc. Perkin Trans. 2, pp. 1136-1141]. The complete mol-ecule is generated by -42m symmetry, with one quarter of a mol-ecule [one N atom (site symmetry m), two C atoms (one with site symmetry m a ...[more]

PMID: 24764981

Similar Datasets

Crystal structure of the co-crystalline adduct 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]dodecane (TATD)-4-bromo-phenol (1/2).

Project description:The structure of the 1:2 co-crystalline adduct C8H16N4·2C6H5BrO, (I), from the solid-state reaction of 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]dodecane (TATD) and 4-bromo-phenol, has been determined. The asymmetric unit of the title co-crystalline adduct comprises a half mol-ecule of aminal cage polyamine plus a 4-bromo-phenol mol-ecule. A twofold rotation axis generates the other half of the adduct. The primary inter-species association in the title compound is through two inter-molecular O-H⋯N hydrogen bonds. In the crystal, the adducts are linked by weak non-conventional C-H⋯O and C-H⋯Br hydrogen bonds, giving a two-dimensional supra-molecular structure parallel to the bc plane.

| S-EPMC4420134 | biostudies-literature

Crystal structure of the co-crystalline adduct 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.1(3,8)]dodecane (TATD)-4-chloro-3,5-di-methyl-phenol (1/1).

Project description:In the crystal of the title co-crystalline adduct, C8H16N4·C8H9ClO, (I), prepared by solid-state reaction, the mol-ecules are linked by inter-molecular O-H⋯N hydrogen bonds, forming a D motif. The aza-adamantane structure in (I) is slightly distorted, with N-CH2-CH2-N torsion angles of 10.4 (3) and -9.0 (3)°. These values differ slightly from the corresponding torsion angles in the free aminal cage (0.0°) and in related co-crystalline adducts, which are not far from a planar geometry and consistent with a D 2d mol-ecular symmetry in the tetra-aza-tri-cyclo structure. The structures also differ in that there is a slight elongation of the N-C bond lengths about the N atom that accepts the hydrogen bond in (I) compared with the other N-C bond lengths. In the crystal, the two mol-ecules are not only linked by a classical O-H⋯N hydrogen bond but are further connected by weak C-H⋯π inter-actions, forming a two-dimensional supra-molecular network parallel to the bc plane.

| S-EPMC4518940 | biostudies-literature

Aqua-(1,4,7,10-tetra-aza-cyclo-dodeca-ne)zinc(II) bis-(perchlorate).

Project description:The cationic ZnII part of aqua-(1,4,7,10-tetra-aza-cyclo-dodeca-ne)zinc(II) bis-(perchlorate), [Zn(C8H20N4)(H2O)](ClO4)2, exhibits a slightly distorted square-pyramidal coordination environment with a water mol-ecule in the apical position. In the crystal, the macrocyclic ring alternates between two conformations with equal occupancies. Two of the three perchlorate anions are situated about a twofold rotation axis, and one of them shows disorder of the O atoms with occupancies of 0.62 (7) and 0.38 (7). In the crystal, the complexes are connected by inter-molecular hydrogen bonding via the perchlorate anions.

| S-EPMC9462334 | biostudies-literature

Crystal structure of the co-crystalline adduct 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.13,8]dodecane (TATD)-4-iodo-phenol (1/2): supra-molecular assembly mediated by halogen and hydrogen bonding.

Project description:The asymmetric unit of the title co-crystalline adduct, 1,3,6,8-tetra-aza-tri-cyclo[4.4.1.13,8]dodecane (TATD)-4-iodo-phenol (1/2), C8H16N4·2C6H5IO, comprises a half mol-ecule of the aminal cage polyamine plus a 4-iodo-phenol mol-ecule. A twofold rotation axis generates the other half of the adduct. The components are linked by two inter-molecular O-H⋯N hydrogen bonds. The adducts are further linked into a three-dimensional framework structure by a combination of N⋯I halogen bonds and weak non-conventional C-H⋯O and C-H⋯I hydrogen bonds.

| S-EPMC5683492 | biostudies-literature

Crystal structure of the 1:2 co-crystal of 1,3,6,8-tetra-aza-tri-cyclo-[4.3.1.13,8]undecane (TATU) and 4-chloro-phenol (1/2).

Project description:In the title compound, C7H14N4·2C6H5ClO, which crystallized with two crystallographically independent 4-chloro-phenol mol-ecules and one 1,3,6,8-tetra-aza-tri-cyclo-[4.3.1.13,8]undecane (TATU) mol-ecule in the asymmetric unit, the independent components are linked by two O-H⋯N hydrogen bonds. The hydrogen-bond acceptor sites are two non-equivalent N atoms from the aminal cage structure, and the tricyclic system distorts by changing the C-N bond lengths. In the crystal, these hydrogen-bonded aggregates are linked into chains along the c axis by C-H⋯N hydrogen bonds. The crystal structure also features C-H⋯π contacts.

| S-EPMC5095853 | biostudies-literature

(1S,3S,8R,9S,10R)-9,10-Ep-oxy-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodeca-ne.

Project description:The title compound, C16H26O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-ene with meta-chloro-perbenzoic acid. The mol-ecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.

| S-EPMC3998592 | biostudies-literature

Mechanochemical synthesis and crystal structure of a 1:2 co-crystal of 1,3,6,8-tetra-aza-tri-cyclo[4.3.1.13,8]undecane (TATU) and 4-chloro-3,5-dimethyl-phenol.

Project description:Solvent-free treatment of 1,3,6,8-tetra-aza-tri-cyclo-[4.3.1.13,8]undecano (TATU) with 4-chloro-3,5-di-methyl-phenol led to the formation of the title co-crystal, C7H14N4·2C8H9ClO. The asymmetric unit contains one aminal cage mol-ecule and two phenol mol-ecules linked via two O-H⋯N hydrogen bonds. In the aminal cage, the N-CH2-CH2-N unit is slightly distorted from a syn periplanar geometry. Aromatic π-π stacking between the benzene rings from two different neighbouring phenol mol-ecules [centroid-centroid distance = 4.0570 (11) Å] consolidates the crystal packing.

| S-EPMC5095854 | biostudies-literature

First hydrogen-bonded adduct of sterically hindered 2-tert-butyl-4-methyl-phenol (TBMP) with 1,3,6,8-tetra-aza-tri-cyclo-[4.4.1.13,8]dodecane (TATD) via coupling of classical hydrogen bonds and C-H⋯π non-covalent inter-actions.

Project description:The title compound, C8H16N4·2C11H16O, was synthesized from the corres-ponding sterically crowded phenol by treatment with the aminal cage polyamine. Single-crystal X-ray diffraction structural analysis revealed the three-mol-ecule aggregate to crystallize in the monoclinic space group P2/c with one half of a 1,3,6,8-tetra-aztri-cyclo-[4.4.1.13,8]dodecane (TATD) mol-ecule and one 2-tert-butyl-4-methyl-phenol mol-ecule per asymmetric unit. The crystal structure features inter-molecular O-H⋯N and C-H⋯O hydrogen bonds, as well as inter-molecular C-H⋯π inter-actions.

| S-EPMC9431775 | biostudies-literature

Diaqua-(1,4,8,11-tetra-aza-cyclo-tetra-deca-ne)nickel(II) fumarate tetra-hydrate.

Project description:The asymmetric unit of the title complex salt, [Ni(C(10)H(24)N(4))(H(2)O)(2)](C(4)H(2)O(4))·4H(2)O, comprises half of a nickel(II) complex dication, half of a fumarate dianion and two water mol-ecules. Both the Ni(II) cation and fumarate anion lie on a crystallographic inversion center. The Ni(II) ion in the cyclam complex is six-coordinated within a distorted N(4)O(2) octa-hedral geometry, with the four cyclam N atoms in the equatorial plane and the two water mol-ecules in apical positions. The six-membered metalla ring adopts a chair conformation, whereas the five-membered ring exists in a twisted form. In the crystal packing, inter-molecular O-H⋯O hydrogen bonds between the water molecules and the carboxyl groups of the fumarate anions lead to the formation of layers with R(4) (2)(8) ring motifs. Ni(II) complex cations are sandwiched between two such layers, being held in place by O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds, consolidating a three-dimensional network.

| S-EPMC3007087 | biostudies-literature

4,10-Diformyl-2,6,8,12-tetra-nitro-2,4,6,8,10,12-hexa-azatetra-cyclo-[5.5.0.0.0]dodeca-ne.

Project description:The title compound TNDFIW, C(8)H(8)N(10)O(10), is a caged heterocycle substituted with four nitro and two formyl groups. It is related to the hexa-azaisowurtzitane family of high-density high-energy polycyclic cage compounds. Four nitro groups are appended to the four N atoms of the two five-membered rings, while the other two formyl groups are attached to the two N atoms of the six-membered ring, which adopts a boat conformation. The compound has a cage structure which is constructed from one six-membered and two five-membered rings which are closed by a C-C bond, thus creating two seven-membered rings. There are a number of close intermolecular contacts [O⋯O = 2.827 (5), 2.853 (4) and 2.891 (5) Å; O⋯N = 2.746 (2) and 2.895 (2) Å] The calculated density of TNDFIW is 1.891 Mg m(-3).

| S-EPMC2979879 | biostudies-literature

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