Abstract
The asymmetric unit of the title compound, C17H16N4O6, contains two independent mol-ecules (A and B). The two benzene rings are twisted by an angle of 79.14 (7)° in mol-ecule A, whereas, in mol-ecule B, they are inclined by 19.02 (14)°. The conformations of the mol-ecules are stabilized by intra-molecular N-H⋯O hydrogen bonds between the amide nitro-gen atom and the O atom of the ortho-nitro substituent on the phenyl ring, enclosing an S(6) ring motif. In the amide and aliphatic segments, all the N-H, C=O and C-H bonds are anti to each other. In the crystal, the A and B mol-ecules are linked by inter-molecular amide-to-amide N-H⋯O hydrogen bonds, resulting in chains running along the b-axis direction. The inter-molecular inter-actions were analysed using Hirshfeld surface analysis. The two-dimensional fingerprint plots of the inter-molecular contacts indicate that the major contributions are from H⋯H and O⋯H inter-actions.
Highlights
Alkanediamide derivatives are known to possess a variety of biological activities
The conformation of the nearest C O group is anti to the orthonitro group in the aniline ring in one half of each molecule, as indicated by the torsion angles of À159.5 (3) and À161.9 (3) for C2—C1—N1—C7 and C19—C18—N5—C24, respectively
The O atoms of the ortho-substituted nitro groups attached to the C1/C6 and C18/C23 phenyl rings form short intramolecular contacts, each of 2.01 (3) A, with the nearest amide N atom, forming an N—HÁ Á ÁO contact resulting in an S(6) hydrogen bonding motif
Summary
Alkanediamide derivatives are known to possess a variety of biological activities. There has been a study on the influence of the length of the connecting chain on the antimalarial activity of bisquinolines (Raynes et al, 1995) and OER (oxygen evolution rate) inhibiting activity in spinach in a series of N,N0-bis(3,4-dichlorophenyl)alkanediamides (Kubicova et al, 2000a,b). Structural commentary The asymmetric unit of the title compound (I) contains two independent molecules (designated as A and B in Fig. 1), and four molecules in the unit cell The conformation of the nearest C O group is anti to the orthonitro group in the aniline ring in one half of each molecule, as indicated by the torsion angles of À159.5 (3) and À161.9 (3) for C2—C1—N1—C7 and C19—C18—N5—C24, respectively. In molecule A, the bis-amide group forms dihedral angles of 24.79 (12) and 55.04 (7) with the phenyl rings C1–C6 and C12–C17, respectively. In molecule B, the plane of the amide group forms dihedral angles of 34.24 (13). The O atoms of the ortho-substituted nitro groups attached to the C1/C6 and C18/C23 phenyl rings form short intramolecular contacts, each of 2.01 (3) A , with the nearest amide N atom, forming an N—HÁ Á ÁO contact resulting in an S(6) hydrogen bonding motif
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