Dimethyl 6,6'-dicyano-2,2'-bipyridine-3,3'-dicarboxyl-ate

Area of Science:

• Crystallography
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and designing new materials.
• Pyridine-containing compounds are prevalent in pharmaceuticals, materials science, and coordination chemistry.
• Intermolecular interactions, such as hydrogen bonding and pi-pi stacking, play a significant role in the self-assembly and stability of crystal structures.

Purpose of the Study:

• To elucidate the detailed crystal structure of the title compound, C(16)H(10)N(4)O(4).
• To analyze the conformational aspects, including the twisting of pyridine rings and the orientation of ester groups.
• To identify and characterize the intermolecular forces responsible for stabilizing the crystal lattice.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the precise atomic coordinates and unit cell parameters.
• Crystallographic analysis software was used to analyze bond lengths, bond angles, and dihedral angles.
• Analysis of intermolecular interactions, including hydrogen bonds and pi-pi stacking, was performed using established crystallographic criteria.

Main Results:

• The crystal structure of C(16)H(10)N(4)O(4) was successfully determined.
• The two pyridine rings in the molecule display a significant twist, with a dihedral angle of 44.41(2)° between them.
• Ester groups exhibit dihedral angles of 48.77(4)° and 45.75(2)° relative to their respective pyridine rings.
• The crystal packing is stabilized by intermolecular C-H⋯O hydrogen bonds.
• Interactions involving pi-pi stacking between pyridine rings were observed, with a centroid-to-centroid distance of 3.797(2) Å.

Conclusions:

• The title compound possesses a unique three-dimensional architecture characterized by twisted pyridine rings and specific ester group orientations.
• Intermolecular C-H⋯O hydrogen bonds and pi-pi stacking interactions are key stabilizing forces in the crystal structure.
• The detailed structural information provides a foundation for understanding the compound's physical and chemical properties and potential applications.