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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.

Rivera A, Osorio HJ, Uribe JM, Ríos-Motta J, Bolte M - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The hydrogen-bond formation to one of the N atoms is enough to induce structural stereoelectronic effects in the normal donor→acceptor direction.The dihedral angles between the planes of the nitro group and the attached benzene rings are 4.04 (17) and 5.79 (17)°.Additional C-H⋯O inter-molecular hydrogen-bonding inter-actions form a second supra-molecular inversion dimer with an R 2 (2)(10) motif.

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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 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.

No MeSH data available.


The hydrogen-bonded inversion dimer displaying an (10) motif in the crystal of the title compound, with hydrogen bonds drawn as dashed lines. [Symmetry code: (ii) −x + 1, −y + 1, −z + 1.]
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fig3: The hydrogen-bonded inversion dimer displaying an (10) motif in the crystal of the title compound, with hydrogen bonds drawn as dashed lines. [Symmetry code: (ii) −x + 1, −y + 1, −z + 1.]

Mentions: In the crystal structure of (I), two 1:2 adducts are linked to one another by C26—H26⋯O13i bond pairs (Table 1 ▸) so that an inversion dimer is formed (Table 1 ▸ and Fig. 2 ▸), which displays an (32) motif (Bernstein et al., 1995 ▸). The hydrogen bond with atom C6 as the donor firms an inversion dimer, generating forming a zigzag chain running parallel to [111] through a second C6—H6A⋯O23iv hydrogen bond (Table 1 ▸ and Fig. 4 ▸). Additional C5—H5A⋯O11ii inter­molecular hydro­gen-bonding inter­actions form a second supra­molecular inversion dimer with an (10) motif (Fig. 3 ▸). Both dimers are further linked by a weak inter­molecular C25—H25⋯N2v hydrogen bond (Table 1 ▸). These contacts combine to generate a three-dimensional network structure.


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.

Rivera A, Osorio HJ, Uribe JM, Ríos-Motta J, Bolte M - Acta Crystallogr E Crystallogr Commun (2015)

The hydrogen-bonded inversion dimer displaying an (10) motif in the crystal of the title compound, with hydrogen bonds drawn as dashed lines. [Symmetry code: (ii) −x + 1, −y + 1, −z + 1.]
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645038&req=5

fig3: The hydrogen-bonded inversion dimer displaying an (10) motif in the crystal of the title compound, with hydrogen bonds drawn as dashed lines. [Symmetry code: (ii) −x + 1, −y + 1, −z + 1.]
Mentions: In the crystal structure of (I), two 1:2 adducts are linked to one another by C26—H26⋯O13i bond pairs (Table 1 ▸) so that an inversion dimer is formed (Table 1 ▸ and Fig. 2 ▸), which displays an (32) motif (Bernstein et al., 1995 ▸). The hydrogen bond with atom C6 as the donor firms an inversion dimer, generating forming a zigzag chain running parallel to [111] through a second C6—H6A⋯O23iv hydrogen bond (Table 1 ▸ and Fig. 4 ▸). Additional C5—H5A⋯O11ii inter­molecular hydro­gen-bonding inter­actions form a second supra­molecular inversion dimer with an (10) motif (Fig. 3 ▸). Both dimers are further linked by a weak inter­molecular C25—H25⋯N2v hydrogen bond (Table 1 ▸). These contacts combine to generate a three-dimensional network structure.

Bottom Line: The hydrogen-bond formation to one of the N atoms is enough to induce structural stereoelectronic effects in the normal donor→acceptor direction.The dihedral angles between the planes of the nitro group and the attached benzene rings are 4.04 (17) and 5.79 (17)°.Additional C-H⋯O inter-molecular hydrogen-bonding inter-actions form a second supra-molecular inversion dimer with an R 2 (2)(10) motif.

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 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.

No MeSH data available.