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Updated: Jun 1, 2026
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
2,7-Bis-(trichloro-meth-yl)-1,8-naphthyridine
Summary
The crystal structure of a C(10)H(4)Cl(6)N(2) compound reveals a near-planar 1,8-naphthyridine ring. Molecules are arranged in an anti-parallel fashion, featuring short chlorine-to-chlorine and chlorine-to-nitrogen contacts.
Area of Science:
- Crystallography
- Materials Science
- Organic Chemistry
Background:
- 1,8-naphthyridine derivatives are important heterocyclic compounds with diverse applications.
- Understanding the solid-state structure of halogenated naphthyridines is crucial for predicting their properties and reactivity.
Purpose of the Study:
- To elucidate the crystal structure of the title compound, C(10)H(4)Cl(6)N(2).
- To analyze the molecular arrangement and intermolecular interactions within the crystal lattice.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of bond lengths, bond angles, and intermolecular contacts.
Main Results:
- The molecule exhibits crystallographic twofold symmetry, with the 1,8-naphthyridine ring being nearly planar (r.m.s. deviation of 0.0002 Å).
- Molecules are stacked anti-parallel along the [001] direction.
- Short intermolecular contacts, including Cl⋯Cl (3.3502 Å) and Cl⋯N (3.2004–3.2220 Å), were identified.
Conclusions:
- The crystal packing is influenced by intermolecular chlorine-chlorine and chlorine-nitrogen interactions.
- The structural data provides a foundation for further studies on the physical and chemical properties of this halogenated 1,8-naphthyridine.
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