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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).

Rivera A, Rojas JJ, Ríos-Motta J, Bolte M - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: 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 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia.

ABSTRACT
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.

No MeSH data available.


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Perspective view of the title compound, with displacement ellipsoids drawn at the 50% probability level. The hydrogen bond is drawn as a dashed line.
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fig1: Perspective view of the title compound, with displacement ellipsoids drawn at the 50% probability level. The hydrogen bond is drawn as a dashed line.

Mentions: The crystal structure of the title compound, (I), has confirmed the presence of a 1:1 co-crystalline adduct. A view of this adduct is shown in Fig. 1 ▸. The asymmetric unit of the title compound contains a 1,3,6,8-tetra­aza­tri­cyclo­[4.4.1.13,8]dodecane (TATD) and a 4-chloro-3,5-di­methyl­phenol mol­ecule linked via an O—H⋯N hydrogen bond, forming a D motif (Bernstein et al., 1995 ▸). As in the 1:2 adduct with 4-bromo­phenol (Rivera, Uribe, Rojas et al., 2015 ▸) and the 1:1 adduct with hydro­quinone (Rivera et al., 2007 ▸), the inter­molecular O—H⋯N hydrogen bond in (I) also leads to a stable supra­molecular structure, but comparison of the title compound with the above-mentioned related structures shows that the three adducts differ in the O⋯N hydrogen-bond distances [2.752 (2) Å in (I), 2.705 (5) Å in the 1:2 adduct and 2.767 (2) Å in the co-crystalline adduct with hydro­quinone], which is in agreement with the differences in the pKa values between the species involved in the hydrogen bond (Majerz et al., 1997 ▸): 4-chloro-3,5-di­methyl­phenol (pKa = 9.76); p-bromo­phenol (pKa = 9.37) and hydro­quinone (pKa = 9.85) (Lide, 2003 ▸).


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).

Rivera A, Rojas JJ, Ríos-Motta J, Bolte M - Acta Crystallogr E Crystallogr Commun (2015)

Perspective view of the title compound, with displacement ellipsoids drawn at the 50% probability level. The hydrogen bond is drawn as a dashed line.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518940&req=5

fig1: Perspective view of the title compound, with displacement ellipsoids drawn at the 50% probability level. The hydrogen bond is drawn as a dashed line.
Mentions: The crystal structure of the title compound, (I), has confirmed the presence of a 1:1 co-crystalline adduct. A view of this adduct is shown in Fig. 1 ▸. The asymmetric unit of the title compound contains a 1,3,6,8-tetra­aza­tri­cyclo­[4.4.1.13,8]dodecane (TATD) and a 4-chloro-3,5-di­methyl­phenol mol­ecule linked via an O—H⋯N hydrogen bond, forming a D motif (Bernstein et al., 1995 ▸). As in the 1:2 adduct with 4-bromo­phenol (Rivera, Uribe, Rojas et al., 2015 ▸) and the 1:1 adduct with hydro­quinone (Rivera et al., 2007 ▸), the inter­molecular O—H⋯N hydrogen bond in (I) also leads to a stable supra­molecular structure, but comparison of the title compound with the above-mentioned related structures shows that the three adducts differ in the O⋯N hydrogen-bond distances [2.752 (2) Å in (I), 2.705 (5) Å in the 1:2 adduct and 2.767 (2) Å in the co-crystalline adduct with hydro­quinone], which is in agreement with the differences in the pKa values between the species involved in the hydrogen bond (Majerz et al., 1997 ▸): 4-chloro-3,5-di­methyl­phenol (pKa = 9.76); p-bromo­phenol (pKa = 9.37) and hydro­quinone (pKa = 9.85) (Lide, 2003 ▸).

Bottom Line: 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 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, Código Postal 111321, Colombia.

ABSTRACT
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.

No MeSH data available.


Related in: MedlinePlus