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Crystal structure of 3-[({2-[bis-(2-hy-droxy-benz-yl)amino]-eth-yl}(2-hy-droxy-benz-yl)amino)-meth-yl]-2-hydroxy-5-methyl-benzaldehyde.

Fonseca AS, Bortoluzzi AJ - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: In the 2-hy-droxy-5-methyl-benzaldehyde group, an intra-molecular S(6) O-H⋯O hydrogen bond is observed between the alcohol and aldehyde functions, and the neighbouring phenol arm participates in an intra-molecular S(6) O-H⋯N hydrogen bond.The third phenol group is involved in a bifurcated intra-molecular hydrogen bond with graph-set notation S(6) for O-H⋯N and O-H⋯O intra-molecular hydrogen bonds between neighbouring amine and phenol arms, respectively.Finally, the fourth phenol group acts as an acceptor in a bifurcated intra-molecular hydrogen bond and also acts as donor in an inter-molecular hydrogen bond, which connects inversion-related mol-ecules into dimers with R 4 (4)(8) ring motifs.

View Article: PubMed Central - HTML - PubMed

Affiliation: Depto. de Química - Universidade Federal de Santa Catarina, 88040-900 Florianópolis, Santa Catarina, Brazil.

ABSTRACT
The non-symmetric title mol-ecule, C32H34N2O5, is based on a tetra-substituted ethyl-enedi-amine backbone. The mol-ecular structure consists of three hy-droxy-benzyl groups and one 2-hy-droxy-5-methyl-benzaldehyde group bonded to the N atoms of the di-amine unit. The ethyl-enedi-amine skeleton shows a regular extended conformation, while the spatial orientation of the phenol arms is governed by hydrogen bonds. In the 2-hy-droxy-5-methyl-benzaldehyde group, an intra-molecular S(6) O-H⋯O hydrogen bond is observed between the alcohol and aldehyde functions, and the neighbouring phenol arm participates in an intra-molecular S(6) O-H⋯N hydrogen bond. The third phenol group is involved in a bifurcated intra-molecular hydrogen bond with graph-set notation S(6) for O-H⋯N and O-H⋯O intra-molecular hydrogen bonds between neighbouring amine and phenol arms, respectively. Finally, the fourth phenol group acts as an acceptor in a bifurcated intra-molecular hydrogen bond and also acts as donor in an inter-molecular hydrogen bond, which connects inversion-related mol-ecules into dimers with R 4 (4)(8) ring motifs.

No MeSH data available.


The mol­ecular structure of (I), with displacement ellipsoids drawn at the 40% probability level.
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fig1: The mol­ecular structure of (I), with displacement ellipsoids drawn at the 40% probability level.

Mentions: Compound (I) is a non-symmetric mol­ecule based on a tetra­substituted ethyl­enedi­amine backbone (Fig. 1 ▶). The structure consists of three hy­droxy­benzyl groups and one 2-hy­droxy-5-methyl­benzaldehyde group bonded to nitro­gen atoms of the di­amine unit. The ethyl­enedi­amine skeleton shows a regular extended ‘zigzag’ conformation [with an N1—C2—C3—N4 torsion angle of 174.78 (13)°], while the pendant phenol arms are randomly oriented but governed by hydrogen bonds (Table 1 ▶). Three intra­molecular hydrogen bonds with an S(6) graph-set motif are observed in the mol­ecular structure of (I) (Fig. 2 ▶). One of these occurs between the neighbouring alcohol and aldehyde groups. In addition, intra­molecular O—H⋯N and O—H⋯O inter­actions, which include bifurcated hydrogen bonds, are observed, involving O—H functions as donors and the amine sites and one phenolic oxygen atom as acceptors. All bond lengths and angles found for (I) are in the expected range for organic compounds (Bruno et al., 2004 ▶).


Crystal structure of 3-[({2-[bis-(2-hy-droxy-benz-yl)amino]-eth-yl}(2-hy-droxy-benz-yl)amino)-meth-yl]-2-hydroxy-5-methyl-benzaldehyde.

Fonseca AS, Bortoluzzi AJ - Acta Crystallogr Sect E Struct Rep Online (2014)

The mol­ecular structure of (I), with displacement ellipsoids drawn at the 40% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257411&req=5

fig1: The mol­ecular structure of (I), with displacement ellipsoids drawn at the 40% probability level.
Mentions: Compound (I) is a non-symmetric mol­ecule based on a tetra­substituted ethyl­enedi­amine backbone (Fig. 1 ▶). The structure consists of three hy­droxy­benzyl groups and one 2-hy­droxy-5-methyl­benzaldehyde group bonded to nitro­gen atoms of the di­amine unit. The ethyl­enedi­amine skeleton shows a regular extended ‘zigzag’ conformation [with an N1—C2—C3—N4 torsion angle of 174.78 (13)°], while the pendant phenol arms are randomly oriented but governed by hydrogen bonds (Table 1 ▶). Three intra­molecular hydrogen bonds with an S(6) graph-set motif are observed in the mol­ecular structure of (I) (Fig. 2 ▶). One of these occurs between the neighbouring alcohol and aldehyde groups. In addition, intra­molecular O—H⋯N and O—H⋯O inter­actions, which include bifurcated hydrogen bonds, are observed, involving O—H functions as donors and the amine sites and one phenolic oxygen atom as acceptors. All bond lengths and angles found for (I) are in the expected range for organic compounds (Bruno et al., 2004 ▶).

Bottom Line: In the 2-hy-droxy-5-methyl-benzaldehyde group, an intra-molecular S(6) O-H⋯O hydrogen bond is observed between the alcohol and aldehyde functions, and the neighbouring phenol arm participates in an intra-molecular S(6) O-H⋯N hydrogen bond.The third phenol group is involved in a bifurcated intra-molecular hydrogen bond with graph-set notation S(6) for O-H⋯N and O-H⋯O intra-molecular hydrogen bonds between neighbouring amine and phenol arms, respectively.Finally, the fourth phenol group acts as an acceptor in a bifurcated intra-molecular hydrogen bond and also acts as donor in an inter-molecular hydrogen bond, which connects inversion-related mol-ecules into dimers with R 4 (4)(8) ring motifs.

View Article: PubMed Central - HTML - PubMed

Affiliation: Depto. de Química - Universidade Federal de Santa Catarina, 88040-900 Florianópolis, Santa Catarina, Brazil.

ABSTRACT
The non-symmetric title mol-ecule, C32H34N2O5, is based on a tetra-substituted ethyl-enedi-amine backbone. The mol-ecular structure consists of three hy-droxy-benzyl groups and one 2-hy-droxy-5-methyl-benzaldehyde group bonded to the N atoms of the di-amine unit. The ethyl-enedi-amine skeleton shows a regular extended conformation, while the spatial orientation of the phenol arms is governed by hydrogen bonds. In the 2-hy-droxy-5-methyl-benzaldehyde group, an intra-molecular S(6) O-H⋯O hydrogen bond is observed between the alcohol and aldehyde functions, and the neighbouring phenol arm participates in an intra-molecular S(6) O-H⋯N hydrogen bond. The third phenol group is involved in a bifurcated intra-molecular hydrogen bond with graph-set notation S(6) for O-H⋯N and O-H⋯O intra-molecular hydrogen bonds between neighbouring amine and phenol arms, respectively. Finally, the fourth phenol group acts as an acceptor in a bifurcated intra-molecular hydrogen bond and also acts as donor in an inter-molecular hydrogen bond, which connects inversion-related mol-ecules into dimers with R 4 (4)(8) ring motifs.

No MeSH data available.