N,N-Dihexyl-4-[2-(4-nitro-phen-yl)vin-yl]aniline.

ABSTRACT: The title compound, C(26)H(36)N(2)O(2), was prepared by Horner olefination of p-dihexyl-amino-benzaldehyde and diethyl p-nitro-benzyl-phospho-nate. It crystallizes with two independent mol-ecules in the asymmetric unit. Both have similar geometries of the ?-systems but the conformations of all hexyl chains are different. Whereas one hexyl chain of the first mol-ecule 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 mol-ecule 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.

SUBMITTER: Schollmeyer D 

PROVIDER: S-EPMC3120587 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature