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

Abstract

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”.