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Solid state conformations of symmetrical aromatic biheterocycles: an X-ray crystallographic investigation

2004; Royal Society of Chemistry; Volume: 3; Issue: 3 Linguagem: Inglês

10.1039/b416553e

1477-0539

Christopher M. Fitchett, Christopher Richardson, Peter J. Steel,

Phenothiazines and Benzothiazines Synthesis and Activities

Accurate, low temperature X-ray crystal structure determinations show that 3,3'-biquinoline (6), 2,2'-biquinazoline (7), 2,2'-biquinoxaline (8), 2,2'-bibenzoxazole (10) and 2,2'-bibenzothiazole (11) all exist in the solid state in centrosymmetric, planar conformations that minimise their dipole moments and maximise both conjugation between the rings and various types of attractive intermolecular associations. In contrast, 4,4'-biquinazoline (9) and 1,1'-bibenzotriazole (12) display non-planar conformations due to repulsive intramolecular interactions.