1-(2,3,4-Trihydroxy-benzyl-idene)thio-semicarbazide

Area of Science:

• Crystallography
• Molecular Chemistry
• Hydrogen Bonding

Background:

• The thio-semicarbazide moiety is a key functional group in various chemical compounds.
• Understanding molecular conformation and intermolecular interactions is crucial for predicting chemical properties.

Purpose of the Study:

• To elucidate the conformational flexibility of the thio-semicarbazide fragment in C(8)H(9)N(3)O(3)S.
• To characterize the intra- and intermolecular hydrogen bonding networks within the crystal structure.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
• Analysis of dihedral angles to quantify the twist of the thio-semicarbazide fragment.
• Identification and analysis of hydrogen bond donors and acceptors.

Main Results:

• Three independent molecules of C(8)H(9)N(3)O(3)S exhibit varying degrees of twist in the thio-semicarbazide fragment (dihedral angles: 7.6(1)°, 11.6(1)°, and 20.7(1)°).
• Intramolecular hydrogen bonds (O-H⋯N and O-H⋯O) were observed within the molecules.
• Intermolecular hydrogen bonds (O-H⋯O, O-H⋯S, and N-H⋯O) involving hydroxyl, amino, and sulfur groups lead to the formation of a layered crystal structure.

Conclusions:

• The thio-semicarbazide fragment displays significant conformational variability in the solid state.
• The observed hydrogen bonding patterns dictate the supramolecular architecture, forming a robust layered motif.
• This structural insight is valuable for the design of novel compounds with tailored properties.