5-(2,3-Dichloro-phen-yl)-2-fluoro-pyridine.

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the solid-state packing of organic molecules is crucial for predicting material properties.
• Halogenated aromatic compounds and pyridine derivatives are important building blocks in medicinal chemistry and materials science.

Purpose of the Study:

• To elucidate the crystal structure and intermolecular interactions of a novel compound containing dichloro-benzene and 2-fluoro-pyridine moieties.
• To investigate the role of non-covalent interactions in the self-assembly of this molecule in the solid state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
• Analysis of intermolecular interactions, including hydrogen bonding and π-π stacking, was performed.

Main Results:

• The crystal structure of C(11)H(6)Cl(2)FN was determined, revealing a dihedral angle of 47.73(3)° between the dichloro-benzene and 2-fluoro-pyridine rings.
• Molecules self-assemble into dimers through C-H⋯N interactions, forming R(2)(2)(12) motifs.
• Extended stacks along the [100] direction were observed, facilitated by π-π interactions with a centroid-centroid distance of 3.8889(3) Å.

Conclusions:

• The crystal packing is governed by a combination of C-H⋯N hydrogen bonding and π-π stacking interactions.
• These non-covalent interactions dictate the formation of dimers and extended molecular stacks, influencing the overall solid-state architecture.
• The findings provide insights into the structure-property relationships of halogenated aromatic and pyridine-containing compounds.