[4-(Trifluoromethyl)phenyl]acetonitrile.

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding intermolecular forces is key to predicting and controlling crystal structures.
• The interplay between electron-withdrawing groups like trifluoromethyl (CF3) and cyano (CN) significantly impacts molecular conformation and interactions.
• Crystal structure analysis provides detailed insights into the spatial arrangement of atoms and molecules, revealing bonding patterns.

Purpose of the Study:

• To determine the precise crystal structure of the title compound, C(9)H(6)F(3)N, at low temperature (123 K).
• To investigate the nature and strength of intermolecular interactions, specifically C-H...F and C-H...N contacts.
• To analyze the influence of the trifluoromethyl (CF3) and cyano (CN) substituents on molecular geometry and crystal packing.

Main Methods:

• Single-crystal X-ray diffraction at 123 K.
• Analysis of intermolecular contacts (C-H...F, C-H...N) and bond distances.
• Examination of molecular conformation, including the Ph-CH(2)CN torsion angle and phenyl ring deformations.

Main Results:

• The crystal structure features molecules linked by C-H...F and C-H...N contacts, with the strongest being 2.58 Å and 2.65 Å, respectively.
• Fluorine atoms in the CF3 group compete with the cyano nitrogen for aromatic hydrogen atoms but show less interaction with methylene hydrogens.
• The phenyl ring displays typical endo angle deformations at the ipso-carbon atoms due to differing electron-withdrawing effects of the CF3 and CH2CN groups.

Conclusions:

• The study elucidates the specific roles of CF3 and CN groups in directing intermolecular interactions within the crystal lattice.
• Observed C-H...F and C-H...N interactions dictate the overall crystal packing and molecular assembly.
• The conformational analysis provides insights into the electronic effects of substituents on molecular geometry.