2,4-Dichloro-N-p-tolyl-benzamide

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
• Crystal structure analysis provides detailed insights into molecular geometry, conformation, and intermolecular interactions.

Purpose of the Study:

• To elucidate the detailed crystal structure of the title compound, C(14)H(11)Cl(2)NO.
• To analyze the planarity of the amide unit and the dihedral angles between the aromatic rings and the amide group.
• To investigate the intermolecular interactions, including hydrogen bonding and pi-pi contacts, that govern the crystal packing.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of bond lengths, bond angles, dihedral angles, and intermolecular contacts was performed.
• Computational methods may have been used for analysis of deviations from planarity.

Main Results:

• The C-N-C(=O)-C amide unit was found to be nearly planar, with a root-mean-square deviation of 0.0317 Å.
• Dihedral angles of 65.93(6)° and 29.45(7)° were observed between the amide unit and the dichloro-benzene and tolyl rings, respectively.
• The two aromatic rings are inclined at an angle of 37.92(6)° to each other.
• N-H⋯O hydrogen bonds form chains along the b-axis, while C-H⋯Cl, C-H⋯O, C-H⋯π, and π-π interactions contribute to the stacking of molecules.

Conclusions:

• The crystal structure reveals a specific spatial arrangement of the dichloro-benzene and tolyl rings relative to the amide core.
• Intermolecular hydrogen bonding and other weak interactions play a significant role in organizing the molecules within the crystal lattice.
• The findings contribute to the understanding of structure-property relationships in related organic compounds.