Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 3 (March 2008)

organic compounds

Acta Cryst. (2008). C64, o123-o127 [ doi:10.1107/S0108270108001595 ]

The 1:1 proton-transfer compounds of 4-(phenyldiazenyl)aniline (aniline yellow) with 3-nitrophthalic, 4-nitrophthalic and 5-nitroisophthalic acids

G. Smith, U. D. Wermuth, D. J. Young and J. M. White

Abstract: The structures of the anhydrous 1:1 proton-transfer compounds of the dye precursor aniline yellow [4-(phenyldiazenyl)aniline], namely isomeric 4-(phenyldiazenyl)anilinium 2-carboxy-6-nitrobenzoate, C₁₂H₁₂N₃⁺·C₈H₄NO₆^-, (I), and 4-(phenyldiazenyl)anilinium 2-carboxy-4-nitrobenzoate, C₁₂H₁₂N₃⁺·C₈H₄NO₆^-, (II), and 4-(phenyldiazenyl)anilinium 3-carboxy-5-nitrobenzoate monohydrate, C₁₂H₁₂N₃⁺·C₈H₄NO₆^-·H₂O, (III), have been determined at 130 K. In (I) the cation has longitudinal rotational disorder. All three compounds have substructures comprising backbones formed through strong head-to-tail carboxyl-carboxylate hydrogen-bond interactions [graph set C(7) in (I) and (II), and C(8) in (III)]. Two-dimensional sheet structures are formed in all three compounds by the incorporation of the 4-(phenyldiazenyl)anilinium cations into the substructures, including, in the cases of (I) and (II), infinite H-N-H to carboxylate O-C-O group interactions [graph set C(6)], and in the case of (III), bridging through the water molecule of solvation. The peripheral alternating aromatic ring residues of both cations and anions give only weakly [pi] -interactive step features which lie between the sheets.

Formula: Two isomers of C₁₂H₁₂N₃⁺·C₈H₄NO₆^-, and C₁₂H₁₂N₃⁺·C₈H₄NO₆^-·H₂O


	Structure factor file (CIF format) (159.0 kbytes) [ doi:10.1107/S0108270108001595/gz3114Isup2.hkl ] Contains datablock I

	Structure factor file (CIF format) (142.9 kbytes) [ doi:10.1107/S0108270108001595/gz3114IIsup3.hkl ] Contains datablock II

	Structure factor file (CIF format) (173.6 kbytes) [ doi:10.1107/S0108270108001595/gz3114IIIsup4.hkl ] Contains datablock III

Notes:

To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

Search: From to Advanced search