2-(4-Chloro-benzamido)-acetic acid

Area of Science:

• Crystallography
• Molecular structure analysis
• Supramolecular chemistry

Background:

• Understanding molecular interactions is crucial for materials science.
• Crystal structure analysis provides insights into intermolecular forces.
• Previous studies have explored hydrogen bonding and π-stacking in organic molecules.

Purpose of the Study:

• To determine the crystal structure of the title molecule, C(9)H(8)ClNO(3).
• To elucidate the intermolecular interactions governing the molecular arrangement in the solid state.
• To investigate the presence and nature of hydrogen bonding and π-π stacking.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the crystal structure.
• Analysis of hydrogen bonding (O-H⋯O and N-H⋯O) was performed.
• π-π stacking interactions were identified and quantified.

Main Results:

• The crystal structure of C(9)H(8)ClNO(3) was successfully determined.
• Adjacent molecules form centrosymmetric dimers through O-H⋯O interactions.
• Dimers are linked by N-H⋯O hydrogen bonds into layers parallel to the bc plane.
• Face-to-face π-stacking interactions between benzene rings were observed with a centroid-centroid distance of 3.6884(8) Å.

Conclusions:

• The crystal packing is dictated by a combination of hydrogen bonding and π-π stacking.
• The observed O-H⋯O and N-H⋯O interactions stabilize the dimeric and layered structures.
• The π-π stacking contributes to the overall molecular arrangement within the layers.