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N,N-Dihexyl-4-[2-(4-nitrophenyl)vinyl]aniline
The title compound, C(26)H(36)N(2)O(2), was prepared by Horner olefination of p-dihexylaminobenzaldehyde and diethyl p-nitrobenzylphosphonate. It crystallizes with two independent molecules in the asymmetric unit. Both have similar geometries of the π-systems but the conformations of all hexyl...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3120587/ https://www.ncbi.nlm.nih.gov/pubmed/21754774 http://dx.doi.org/10.1107/S1600536811016709 |
Sumario: | The title compound, C(26)H(36)N(2)O(2), was prepared by Horner olefination of p-dihexylaminobenzaldehyde and diethyl p-nitrobenzylphosphonate. It crystallizes with two independent molecules in the asymmetric unit. Both have similar geometries of the π-systems but the conformations of all hexyl chains are different. Whereas one hexyl chain of the first molecule shows the typical all-anti conformation, the second is arranged in a gauche-anti-gauche-anti conformation with N—C—C—C, C—C—C—C, C—C—C—C and C—C—C—C torsion angles of −65.1 (4), 167.3 (3), 63.3 (4), and 179.4 (3)°. One of the hexyl chains in the other molecule has an anti-anti-gauche-anti conformation [N—C—C—C, C—C—C—C, C—C—C—C and C—C—C—C torsion angles = 179.6 (3), −179.8 (3), −68.7 (5) and −178.8 (4)°], the other starts with an anti-gauche-gauche sequence. Molecules A and B are composed of five planar subunits. The angle sums around the N atoms are in the range 356 (2)–360.0 (2)°. Torsion angles between these segments do not exceed 4.9 (4)°, except for one of the alkyl chains each [molecule A = 26.2 (4)°; molecule B = −6.0 (4)°]. The high planarity of the molecules and the short aniline C—N bonds [1.385 (3) Å in molecule A and 1.378 (3) Å in molecule B] indicate a strong electronic coupling through the stilbene unit. One methylene group is disordered over two positions with an occupancy ratio of 0.72:0.28. |
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