In the title zwitterion, C 16 H 11 FN 2 O, which belongs to the family of azo dyes, the dihedral angle between the benzene ring and the naphthalene ring system is 15.33 (7) and an intramolecular N-HÁ Á ÁO hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by weak C-HÁ Á ÁO hydrogen bonds generate R 2 2 (16) loops. Aromatic -stacking [centroid-centroid distance = 3.585 (11) Å ] is also observed.
Structure descriptionThe structures and properties of azo dyes (solubility, habit, stability, colour) are dependent on their solid-state structures (Kennedy et al., 2004). As part of our studies in this area, we now describe the structure of the title compound, which shows zwitterionic behaviour (i.e. proton transfer from the naphthol group to the azo group) in the solid state.The dihedral angle between the benzene ring and the naphthalene ring system is 15.33 (7) and an intramolecular N-HÁ Á ÁO hydrogen bond ( Fig. 1 and Table 1) closes an S(6) ring. In the crystal, inversion dimers linked by weak C-HÁ Á ÁO hydrogen bonds generate R 2 2 (16) loops. The dimers are linked through -stacking between the benzene ring and naphthalene ring systems of adjacent molecules, the centroid-centroid distance between the C1-ring and C9-ring being 3.585 (11) Å .
Synthesis and crystallizationThe title compound was obtained through the diazotization of 4-fluoroaniline followed by a coupling reaction with 2-naphthol according to the established procedure (Wang et
In the title complex, [Pd(C17H13N2O2)Cl], the PdIIatom is tetracoordinated by an N and two O atoms of an (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-olate ligand and by a Cl atom, and has a square-planar coordination. In the crystal, molecules are linked by pairs of C—H...Cl hydrogen bonds, forming inversion dimers. The dimers are linkedviaoffset π–π interactions [intercentroid distance = 3.546 (3) Å], forming chains running parallel to [100].
The crystal structure of the title compound, C 16 H 13 N 3 O 3 S, shows that the two independent zwitterions in the asymmetric unit are approximately planar. Intramolecular N-HÁ Á ÁO hydrogen bonds occur and the aromatic rings have a trans configuration with respect to the azo double bond. In the crystal, the molecules are linked via N-HÁ Á ÁO hydrogen bonds and -stacking, forming a three-dimensional supramolecular network, the -stacking interactions between adjacent benzene and naphthalene rings having centroid-to-centroid distances of 3.764 (3) and 3.775 (3) Å .
Recently, azo derivatives have attracted attention because the phenylazo-naphtholate group can provide N,O-bidentate chelation to stabilize transition or main group metal complexes. azo derivatives and their metal complexes are very important pigments for synthetic leather and vinyl polymers. On the other hand, Azo-metal chelates are known to be involved in a number of biological reactions, such as inhibition of DNA, RNA, and protein synthesis, nitrogen fixation, and carcinogenesis. Furthermore, high-density optical data storage has been a subject of extensive research in the past decade.The present work aimed chiefly to throw more light on the Structural characterization of the title mononuclear Co(II). The coordination behaviour of this azo compound towards Co(II) ion is reported using different analytical tools of single crystal X-ray diffraction analysis. Furthermore, the role of weak intermolecular interactions in the crystal packing has been analysed.
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