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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Published on: February 15, 2016

Isoquinolin-5-amine.

Ana María Atria1, Maria Teresa Garland, Ricardo Baggio

  • 1Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Santiago, Chile. aatria@ciq.uchile.cl

Acta Crystallographica. Section C, Crystal Structure Communications
|September 26, 2012
PubMed
Summary

This study details the crystal structure of a C(9)H(8)N(2) compound, revealing an exceptionally planar isoquinoline core. Its supramolecular assembly features interwoven hydrogen-bonded chains stabilized by various weak interactions.

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • The study investigates the structural and crystallographic properties of a specific organic compound.
  • Understanding molecular arrangements in the solid state is crucial for material science and drug design.

Purpose of the Study:

  • To elucidate the detailed crystal structure of the title compound, C(9)H(8)N(2).
  • To analyze the molecular geometry, including planarity and deviations.
  • To characterize the supramolecular assembly and hydrogen bonding network.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the crystal structure.
  • Analysis of intermolecular interactions, including hydrogen bonds (N-H···N, C-H···N) and C-H···π contacts.
  • Calculation of root-mean-square (r.m.s.) deviation to assess planarity.

Main Results:

  • The asymmetric unit contains two nearly identical molecules with highly planar isoquinoline cores (max r.m.s. deviation = 0.014 Å).
  • Amino groups (-NH(2)) exhibit pyramidalization around the nitrogen atom.
  • A supramolecular structure is formed by parallel hydrogen-bonded chains (N-H···N), further linked by weaker C-H···N bonds and C-H···π interactions.

Conclusions:

  • The compound exhibits significant planarity in its isoquinoline core, with notable pyramidalization in the amino groups.
  • The crystal packing is dominated by a robust network of hydrogen bonds and weaker interactions, forming interwoven chains.
  • The findings provide insights into the solid-state behavior and intermolecular forces governing this class of compounds.