Crystal structure of 2-pentyl-oxybenzamide

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the three-dimensional arrangement of molecules in crystals is crucial for predicting material properties.
• Intramolecular and intermolecular interactions dictate crystal packing and stability.
• Hydrogen bonding plays a significant role in organizing molecular structures.

Purpose of the Study:

• To elucidate the crystal structure of the molecule C12H17NO2.
• To investigate the role of intramolecular and intermolecular hydrogen bonding in the molecular assembly.
• To characterize the packing arrangement and the formation of a three-dimensional framework structure.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of bond distances, angles, and dihedral angles provided insights into molecular geometry.
• Identification and analysis of hydrogen bonds (N-H⋯O, C-H⋯O) and C-H⋯π interactions were performed.

Main Results:

• The molecule C12H17NO2 exhibits an intramolecular N-H⋯O hydrogen bond between the amide NH2 group and the pent-yloxy oxygen.
• The benzene ring is oriented with specific dihedral angles relative to the amide and pent-yloxy groups.
• Molecules form inversion dimers linked by N-H⋯O hydrogen bonds, which further assemble into columns stabilized by C-H⋯O and C-H⋯π interactions, creating a 3D framework.

Conclusions:

• The crystal structure of C12H17NO2 is characterized by a specific arrangement driven by intramolecular and intermolecular hydrogen bonding.
• The formation of inversion dimers and their subsequent arrangement into columns highlights the importance of non-covalent interactions in crystal engineering.
• The study provides a detailed understanding of the supramolecular architecture and packing of this organic molecule.