Intermolecular contacts in bromomalonic aldehyde-intuition, experiment, and theory

Mutually perpendicular hydrogen bonds, halogen bonds and stacking interactions are investigated in the seemingly simple crystal structure of bromomalonic aldehyde (C3H3O2Br). This combined experimental and theoretical study sheds new light on the role of electrostatic interactions in molecular crystalline networks and poses a caveat to look beyond what may be termed chemical intuition.