Abstract
The structure of the 1:1 proton-transfer compound of 4-chloroaniline with 4,5-dichlorophthalic acid (DCPA), viz. C6H7ClN+·C8H3Cl2O4 −, has been determined at 130 K. The non-planar hydrogen phthalate anions and the 4-chloroanilinium cations form two-dimensional O—H⋯O and N—H⋯O hydrogen-bonded substructures which have no peripheral extension. Between the sheets there are weak π–π associations between alternating cation–anion aromatic ring systems [shortest centroid–centroid separation = 3.735 (4) Å].
Highlights
C6H7ClN+C8H3Cl2O4, has been determined at 130 K
H atoms treated by a mixture of independent and constrained refinement max = 0.64 e Å3
For the structures of other hydrogen dichlorophthalic acid (DCPA) salts with aromatic Lewis bases showing similar two-dimensional substructures, see: Smith et al (2008b)
Summary
Refinement a School of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia, and bBIO-21 Molecular. Science and Biotechnology, University of Melbourne, Parkville, Victoria 3052, Australia. H atoms treated by a mixture of independent and constrained refinement max = 0.64 e Å3. R factor = 0.062; wR factor = 0.175; data-to-parameter ratio = 10.6. The structure of the 1:1 proton-transfer compound of 4chloroaniline with 4,5-dichlorophthalic acid (DCPA), viz. C6H7ClN+C8H3Cl2O4, has been determined at 130 K. The non-planar hydrogen phthalate anions and the 4-chloroanilinium cations form two-dimensional O—H O and N—. H O hydrogen-bonded substructures which have no peripheral extension. Between the sheets there are weak – associations between alternating cation–anion aromatic ring systems [shortest centroid–centroid separation = 3.735 (4) Å]
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