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Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol
Each of the title dis-symmetric di-Schiff base compounds, C(15)H(12)Cl(2)N(2)O(2) (I) and C(14)H(9)BrCl(2)N(2)O (II), features a central azo-N—N bond connecting two imine groups, each with an E-configuration. One imine bond in each molecule connects to a 2,6-dichlorobenzene substituent while the...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7274017/ https://www.ncbi.nlm.nih.gov/pubmed/32523754 http://dx.doi.org/10.1107/S2056989020006416 |
Sumario: | Each of the title dis-symmetric di-Schiff base compounds, C(15)H(12)Cl(2)N(2)O(2) (I) and C(14)H(9)BrCl(2)N(2)O (II), features a central azo-N—N bond connecting two imine groups, each with an E-configuration. One imine bond in each molecule connects to a 2,6-dichlorobenzene substituent while the other links a 2-hydroxyl-3-methoxy-substituted benzene ring in (I) or a 2-hydroxyl-4-bromo benzene ring in (II). Each molecule features an intramolecular hydroxyl-O—H⋯N(imine) hydrogen bond. The C—N—N—C torsion angles of −151.0 (3)° for (I) and 177.8 (6)° (II) indicates a significant twist in the former. The common feature of the molecular packing is the formation of supramolecular chains. In (I), the linear chains are aligned along the a-axis direction and the molecules are linked by methoxy-C—H⋯O(methoxy) and chlorobenzene-C—Cl⋯π(chlorobenzene) interactions. The chain in (II) is also aligned along the a axis but, has a zigzag topology and is sustained by Br⋯O [3.132 (4) Å] secondary bonding interactions. In each crystal, the chains pack without directional interactions between them. The non-covalent interactions are delineated in the study of the calculated Hirshfeld surfaces. Dispersion forces make the most significant contributions to the identified intermolecular interactions in each of (I) and (II). |
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