4,5-Diazafluoren-9-one benzoylhydrazone monohydrate

Area of Science:

• Crystallography and Molecular Structure
• Organic Chemistry
• Supramolecular Chemistry

Background:

• Understanding the tautomeric forms and stereochemistry of organic compounds is crucial for predicting their properties and reactivity.
• The formation of extended structures through intermolecular interactions, such as hydrogen bonding, influences material properties.

Purpose of the Study:

• To elucidate the solid-state structure and tautomeric form of the title compound, C(18)H(12)N(4)O.H(2)O.
• To investigate the intermolecular interactions and solid-state packing of the compound.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of bond lengths, bond angles, and dihedral angles provided insights into the molecular geometry.
• Hydrogen bonding networks were identified and characterized.

Main Results:

• The title compound crystallizes as a hydrate and adopts the keto tautomeric form.
• The azomethine C=N double bond is confirmed to be in the E configuration.
• A small dihedral angle of 11.3 (1) degrees was observed between the diazafluorene moiety and the phenyl ring.
• Infinite chain-like supramolecular structures are formed via O-H---N hydrogen bonds involving water molecules and the diazafluorene units.

Conclusions:

• The study provides a detailed structural characterization of the title compound in the solid state.
• The keto tautomer and E configuration are established, offering insights into its chemical behavior.
• The observed hydrogen bonding pattern leads to the formation of extended 1D chains, highlighting potential for crystal engineering.