N-(2,6-Dimethyl-phen-yl)-2-(2-thien-yl)acetamide

Area of Science:

• Crystallography
• Organic Chemistry
• Materials Science

Background:

• Understanding the solid-state structure of organic molecules is crucial for predicting their physical and chemical properties.
• The title compound, C(14)H(15)NOS, presents an interesting case for structural analysis due to potential conformational flexibility.

Purpose of the Study:

• To elucidate the crystal structure and molecular conformation of the title compound, C(14)H(15)NOS.
• To investigate the intermolecular interactions governing the self-assembly of the molecules in the crystalline state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
• Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular geometry.
• Intermolecular interactions, including hydrogen bonding and C-H⋯O contacts, were identified and analyzed.

Main Results:

• The thienyl ring in C(14)H(15)NOS exhibits positional disorder, with a major component site-occupancy factor of 0.569(3).
• The molecule displays a highly twisted conformation around the central amide group, evidenced by significant dihedral angles between the thienyl and benzene rings (77.01(15)° and 70.34(18)°).
• In the crystal lattice, molecules self-associate into chains along the [100] direction via N-H⋯O hydrogen bonds, further stabilized by C-H⋯O contacts.

Conclusions:

• The crystal structure of C(14)H(15)NOS is characterized by significant molecular twisting and positional disorder of the thienyl ring.
• The observed self-association into hydrogen-bonded chains dictates the packing arrangement in the solid state.
• These findings contribute to the understanding of structure-property relationships in organic crystalline materials.