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Crystal structure of the 1:2 co-crystal of 1,3,6,8-tetra-aza-tri-cyclo-[4.3.1.1^3,8]undecane (TATU) and 4-chloro-phenol (1/2).

ABSTRACT: 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-[4.3.1.1^3,8]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.

SUBMITTER: Rivera A

PROVIDER: S-EPMC5095853 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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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).

Rivera Augusto A Rojas Jicli José JJ Osorio Héctor Jairo HJ Ríos-Motta Jaime J Bolte Michael M

Acta crystallographica. Section E, Crystallographic communications 20161025 Pt 11

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 changin ...[more]

PMID: 27840728

Similar Datasets

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

Crystal structure of the 1,3,6,8-tetra-aza-tri-cyclo[4.3.1.1(3,8)]undecane (TATU)-4-nitro-phenol (1/2) adduct: the role of anomeric effect in the formation of a second hydrogen-bond inter-action.

Project description:In the title ternary co-crystalline adduct, C7H14N4·2C6H5NO3, mol-ecules are linked by two inter-molecular 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 nitro-phenol mol-ecules 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 supra-molecular dimer enclosing an R 6 (6)(32) ring motif. Additional C-H⋯O inter-molecular hydrogen-bonding inter-actions form a second supra-molecular inversion dimer with an R 2 (2)(10) motif. These units are linked via C-H⋯O and C-H⋯N hydrogen bonds, forming a three-dimensional network.

| S-EPMC4645038 | biostudies-literature

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

Project description: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.

| S-EPMC3998434 | 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-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

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

Racemic methyl 3,10-dioxa-2-aza-tri-cyclo-[6.2.1.0]undecane-4-carboxyl-ate.

Project description:The structure of the racemic title compound, C(10)H(15)NO(4), consists of a tricyclic skeleton comprising a six-membered piperidine ring and five-membered isoxazolidine and tetra-hydro-furan rings. The piperidine ring adopts a distorted chair conformation, while the isoxazolidine and tetra-hydro-furan rings have envelope conformations.

| S-EPMC3089240 | biostudies-literature

1-Hexyl-1,3,6,8-tetra-aza-tricyclo-[4.3.1.1]undecan-1-ium iodide.

Project description:In the title compound, C(13)H(27)N(4) (+)·I(-), the ethyl-ene bridge is distorted from the ideal D(2d) symmetry wherein an N-C-C-N planar bridge, around whose C-C bond the C-N and C-H bonds are exactly eclipsed, is disordered over two sites with equal occupancies. In both disorder components, the hexyl chain adopts an ideal all-trans conformation. In the crystal, adjacent ions are connected by C-H⋯I hydrogen bonds, forming ionic pairs that are further linked into chains along [101] via a second C-H⋯I inter-action.

| S-EPMC3254358 | 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

Crystal structure of di-aqua-(3,14-diethyl-2,6,13,17-tetra-aza-tri-cyclo-[16.4.0.07,12]docosa-ne)copper(II) dichloride tetra-hydrate.

Project description:The crystal structure of the novel hydrated CuII salt, [Cu(L)(H2O)2]Cl2·4H2O (L = 3,14-diethyl-2,6,13,17-tetra-aza-tri-cyclo-[16.4.0.07,12]docosane, C22H44N4) has been determined using synchrotron radiation. The asymmetric unit contains one half of the [Cu(L)(H2O)2]2+ cation (completed by crystallographic inversion symmetry), one chloride anion and two lattice water mol-ecules. The copper(II) atom exists in a tetra-gonally distorted octa-hedral environment with the four N atoms of the macrocyclic ligand in equatorial and two O atoms from water mol-ecules in axial positions. The latter exhibit a long axial Cu-O bond length of 2.7866 (16) Å due to the Jahn-Teller distortion. The macrocyclic ring adopts a stable trans-III conformation with typical Cu-N bond lengths of 2.0240 (11) and 2.0441 (3) Å. The complex is stabilized by hydrogen bonds formed between the O atoms of coordinated water mol-ecules and the NH groups as donors, and chloride anions as acceptors. The chloride anions are further connected to the lattice water solvent molecules through O-H⋯Cl hydrogen bonds, giving rise to a three-dimensional network structure.

| S-EPMC8100274 | biostudies-literature