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11:01
Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase
Published on: November 23, 2016
N-(2,6-Dimethyl-phen-yl)-2-methyl-benzamide
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
This study details the molecular structure of C(16)H(17)NO, revealing specific anti-periplanar conformations and dihedral angles. Molecular packing is influenced by N-H⋯O hydrogen bonds, forming chains in the crystal structure.
Area of Science:
- Organic Chemistry
- Crystallography
- Molecular Structure
Background:
- Understanding the conformational preferences and intermolecular interactions of organic molecules is crucial in chemistry.
- Related compounds often exhibit similar conformational arrangements, providing a basis for comparison.
- Amide groups and substituted phenyl rings are common structural motifs in organic chemistry.
Purpose of the Study:
- To elucidate the detailed molecular conformation of the title compound, C(16)H(17)NO.
- To investigate the dihedral angles between the amide group and the phenyl rings.
- To characterize the intermolecular interactions and crystal packing of the molecule.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.
- Conformational analysis was performed to describe the spatial arrangement of atoms.
- Hydrogen bonding interactions were identified and analyzed.
Main Results:
- The N-H and C=O groups adopt an anti-periplanar conformation, consistent with related structures.
- The C=O group exhibits a syn conformation relative to the methyl substituent on the 2-methyl-phenyl ring.
- Dihedral angles of 50.3(3)° and 64.6(3)° were measured between the amide group and the 2-methyl-phenyl and 2,6-dimethyl-phenyl rings, respectively.
- The angle between the two phenyl rings is 14.26(7)°.
- Molecules are arranged in chains through N-H⋯O hydrogen bonds, with an additional intramolecular C-H⋯O hydrogen bond observed.
Conclusions:
- The study provides a precise description of the molecular geometry and conformation of C(16)H(17)NO.
- The observed hydrogen bonding patterns dictate the crystal packing, leading to chain formation.
- The findings contribute to the understanding of structure-property relationships in related organic compounds.
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