The crystal structure of (E)-2-ethyl-N-(4-nitro-benzyl-idene)aniline: three-dimensional supra-molecular assembly mediated by C-H⋯O hydrogen bonds and nitro⋯π(arene) inter-actions.

Christopher Glidewell,Belakavadi K Sagar,Hemmige S Yathirajan,Marisiddaiah Girisha,Ravindranath S Rathore

doi:10.1107/s2056989018009544

Christopher Glidewell, Belakavadi K Sagar + Show 3 more

Open Access

https://doi.org/10.1107/s2056989018009544

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Abstract

In the mol-ecule of the title compound, C15H14N2O2, the 2-ethyl-phenyl group is disordered over two sets of atomic sites having occupancies of 0.515 (19) and 0.485 (19), and the dihedral angle between the two partial-occupancy aryl rings is 6(2)°. A combination of C-H⋯O hydrogen bonds and nitro⋯π(arene) inter-actions links the mol-ecules into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds.

Highlights

In the molecule of the title compound, C15H14N2O2, the 2-ethylphenyl group is disordered over two sets of atomic sites having occupancies of 0.515 (19) and 0.485 (19), and the dihedral angle between the two partial-occupancy aryl rings is 6(2)
In view of the general importance of Schiff bases, and in a continuation of our own structural study of compounds of this type (Girisha et al, 2017, 2018) we report here the molecular and supramoleuclar structure of (E)-2-ethyl-N-(4-nitrobenzylidene)aniline (I) (Fig. 1), where the ethyl group turns out to be disordered over two sets of atomic sites and where the molecules are linked into a three-dimensional supramolecular array
D—HÁ Á ÁA 167 adjacent aryl ring, with a dihedral angle of only 8.3 (2) between these two units; on the other hand, the dihedral angles between the nitrated aryl ring and the major and minor components of the disordered ring are 36.7 (10) and 42.6 (11), respectively

Summary

Chemical context

Schiff bases exhibit a very wide range of biological activities (da Silva et al, 2011) and are of interest because of their photochromic and thermochromic properties (Hadjoudis & Mavridis, 2004; Minkin et al, 2011). In view of the general importance of Schiff bases, and in a continuation of our own structural study of compounds of this type (Girisha et al, 2017, 2018) we report here the molecular and supramoleuclar structure of (E)-2-ethyl-N-(4-nitrobenzylidene)aniline (I) (Fig. 1), where the ethyl group turns out to be disordered over two sets of atomic sites and where the molecules are linked into a three-dimensional supramolecular array

Structural commentary

Supramolecular features

Database survey

Synthesis and crystallization

Refinement