Three quinolone compounds featuring O...I halogen bonding.
Ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate, C14H14INO3, (I), and ethyl 1-cyclopropyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate, C15H14INO3, (II), have isomorphous crystal structures, while ethyl 1-dimethylamino-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate, C14H15IN2O3, (III), possesses a different solid-state supramolecular architecture. In all three structures, O...I halogen-bonding interactions connect the quinolone molecules into infinite chains parallel to the unique crystallographic b axis. In (I) and (II), these molecular chains are arranged in (101) layers, via pi-pi stacking and C-H...pi interactions, and these layers are then interlinked by C-H...O interactions. The structural fragments involved in the C-H...O interactions differ between (I) and (II), accounting for the observed difference in planarity of the quinolone moieties in the two isomorphous structures. In (III), C-H...O and C-H...pi interactions form (100) molecular layers, which are crosslinked by O...I and C-H...I interactions.
Bauer
Jurica
J
GlaxoSmithKline Research Centre Zagreb, Prilaz Baruna Filipovića 29, HR-10000 Zagreb, Croatia.
Milić
Dalibor
D
Modrić
Marina
M
D018360:Crystallography, X-Ray; D003521:Cyclopropanes / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D008958:Models, Molecular; D011804:Quinolines / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry*
D003521:Cyclopropanes; D006219:Halogens; D011804:Quinolines; D015363:Quinolones; C544645:ethyl 1-cyclopropyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate; C544644:ethyl 1-ethyl-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate; D007455:Iodine