Structural Variability in the Monofluoroethynylbenzenes Mediated through Interactions Involving “Organic” Fluorine

Citations Over TimeTop 10% of 2011 papers

Abstract

Competition among weak intermolecular interactions can lead to polymorphism, the appearance of various crystalline forms of a substance with comparable cohesive energies. The crystal structures of 2-fluorophenylacetylene (2FPA) and 3-fluorophenylacetylene (3FPA), both of which are liquids at ambient conditions, have been determined by in situ cryocrystallization. Both compounds exhibit dimorphs, with one of the forms observed in common, P21, Z = 2 and the other form being Pna21, Z = 4 for 2FPA and P21/c, Z = 12 for 3FPA. Variations in the crystal structures of the dimorphs of each of these compounds arise from subtle differences in the way in which weak intermolecular interactions such as C–H···π and C–H···F are manifested. The interactions involving “organic” fluorine, are entirely different from those in the known structure of 4-fluorophenylacetylene (4FPA), space group P21/c, Z = 4. The commonalities and differences in these polymorphs of 2FPA and 3FPA have been analyzed in terms of supramolecular synthons and extended long-range synthon aufbau module (LSAM) patterns. These structures are compared with the three polymorphs of phenylacetylene, in terms of the T-shaped C–H···π interaction, a feature common to all these structures.

Related Papers

• → Role of supramolecular synthons in the formation of the supramolecular architecture of molecular crystals revisited from an energetic viewpoint(2014)81 cited
• → Supramolecular aggregation patterns based on the bio-inspired Se(lone pair)⋯π(aryl) synthon(2011)42 cited
• → Extending Primary Ammonium Dicarboxylate (PAD) to Diprimary Ammonium Dicarboxylate (DPAD) Synthon and Its Implication in Supramolecular Gelation(2013)12 cited
• → Role of S…O non-bonded interaction in controlling supramolecular assemblies in a new series of 2-aminobenzothiazole based organic salts/ co-crystals(2018)11 cited
• → Supramolecular synthons and pattern recognition in adenine amides – synthesis, structures and thermal properties(2015)1 cited