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Area of Science:

  • Crystallography
  • Materials Science
  • Supramolecular Chemistry

Background:

  • 1551 homomolecular hydrogen-bonded frameworks in organic crystals are classified into 148 topological types.
  • Hydrogen-bonded frameworks can be represented as nets of molecular centroids, edges, or rings.
  • The influence of hydrogen bonds on molecular packing topology requires investigation.

Purpose of the Study:

  • To determine if hydrogen bonding affects the topology of molecular packings in organic crystals.
  • To analyze the hydrogen-bond patterns formed by molecules not related by symmetry.
  • To propose rules for the rational design of molecular frameworks.

Main Methods:

  • Classification of 1551 homomolecular hydrogen-bonded frameworks into topological types.
  • Analysis of 42,270 molecular crystals lacking hydrogen bonds to assess topology independence.
  • Examination of 231 homomolecular frameworks with crystallographically distinct molecules.

Main Results:

  • The topology of molecular packings in organic crystals is independent of hydrogen bonding.
  • Molecules not related by symmetry exhibit a tendency to form identical hydrogen-bond patterns.
  • Relationships between net topological types, space-group symmetry, site symmetry, and molecular point-group symmetry were discussed.

Conclusions:

  • Hydrogen bonding does not dictate the overall topology of molecular frameworks.
  • Symmetry and molecular properties influence hydrogen-bond pattern formation.
  • A set of rules for crystal engineering of molecular frameworks has been proposed.