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N-(2-Pyridylmeth-yl)phthalimide.

Olga Garduño-Beltrán¹, Perla Román-Bravo, Felipe Medrano

¹Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos. Av. Universidad 1001 Col., Chamilpa, CP 62209, Cuernavaca Mor., Mexico.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

The crystal structure of C(14)H(10)N(2)O(2) reveals phthalimide and 2-pyridylmethyl groups nearly perpendicular. Molecules form chains via C-H⋯O interactions, stabilized by π-π stacking between pyridine rings.

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Area of Science:

Crystallography
Organic Chemistry
Supramolecular Chemistry

Background:

Understanding molecular arrangements in crystals is crucial for predicting material properties.
Phthalimide and pyridine derivatives are common scaffolds in medicinal chemistry and materials science.

Purpose of the Study:

To elucidate the crystal structure and intermolecular interactions of the title compound, C(14)H(10)N(2)O(2).
To investigate the packing motifs and stabilizing forces within the crystal lattice.

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the three-dimensional molecular structure.
Analysis of intermolecular contacts, including hydrogen bonds and π-π interactions, was performed.

Main Results:

The crystal structure of C(14)H(10)N(2)O(2) was determined, showing phthalimide and 2-pyridylmethyl units with an inter-planar angle of 85.74(2)°.
Molecules are organized into chains along the b axis through weak C-H⋯O interactions.
Offset π-π interactions between adjacent pyridine rings (centroid-centroid distance of 3.855(2) Å) further stabilize the crystal packing.

Conclusions:

The crystal structure highlights a near-perpendicular orientation between the phthalimide and 2-pyridylmethyl moieties.
The observed intermolecular interactions, C-H⋯O hydrogen bonds and π-π stacking, dictate the supramolecular assembly and crystal stability.