N-(o-chlorophenyl)-2,5-dimethylpyrrole-3-carbaldehyde

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure

Background:

• Understanding the solid-state behavior of organic compounds is crucial for predicting their physical and chemical properties.
• The title compound, C(13)H(12)ClNO, presents an interesting case for structural analysis due to potential conformational variations.
• Previous studies on similar heterocyclic aldehydes have highlighted the impact of substituent groups on ring geometry and intermolecular interactions.

Purpose of the Study:

• To elucidate the detailed crystal structure of the title compound, C(13)H(12)ClNO.
• To investigate the conformational differences among independent molecules in the asymmetric unit.
• To identify and characterize intermolecular interactions, such as hydrogen bonds and C-H.pi interactions, and their influence on molecular packing.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional structure of the compound.
• Crystallographic data were analyzed to identify independent molecules and assess conformational variations.
• Intermolecular interactions, including hydrogen bonds and C-H.pi interactions, were geometrically analyzed.

Main Results:

• Three crystallographically independent molecules of C(13)H(12)ClNO were identified in the asymmetric unit.
• Significant conformational differences were observed in the orientation of phenyl rings relative to pyrrole rings.
• Intermolecular C-H.O hydrogen bonds and C-H.pi interactions were characterized, influencing molecular arrangement and stability.

Conclusions:

• The crystal structure of C(13)H(12)ClNO is characterized by multiple independent molecules with distinct phenyl-pyrrole ring orientations.
• The coplanar aldehyde groups impact pyrrole ring geometry, leading to elongated C-C and C-N bonds.
• Intermolecular hydrogen bonding and C-H.pi interactions play a significant role in the observed crystal packing and molecular stabilization.