(Z)-1-(2,5-Dichloro-3-thien-yl)ethanone semicarbazone

Area of Science:

• Crystallography
• Chemical Physics
• Materials Science

Background:

• Understanding molecular structure and intermolecular forces is crucial for predicting material properties.
• Crystal engineering relies on identifying and utilizing specific interactions to design materials with desired characteristics.

Purpose of the Study:

• To elucidate the crystal structure of the title molecule, C(7)H(7)Cl(2)N(3)OS.
• To investigate the nature and significance of intermolecular and intramolecular interactions within the crystal lattice.
• To characterize the self-assembly behavior of the molecule in the solid state.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
• Analysis of crystallographic data was performed to identify and quantify various non-covalent interactions, including hydrogen bonds and π-π stacking.
• Geometric parameters such as bond lengths, bond angles, and deviations from planarity were precisely measured.

Main Results:

• The molecule C(7)H(7)Cl(2)N(3)OS exhibits an approximately planar conformation with a maximum deviation of 0.062(1) Å.
• Short intermolecular distances between the centroids of five-membered rings (3.5340(8) Å) suggest the presence of significant π-π interactions.
• A notable intramolecular Cl⋯N interaction was observed with a distance of 3.0015(11) Å.
• Intermolecular N-H⋯O hydrogen bonds link molecules into R(2)(2)(8) ring motifs.
• Further stabilization is achieved through N-H⋯O hydrogen bonds and C-H⋯O contacts, forming R(2)(1)(7) ring motifs.
• These interactions collectively lead to the formation of molecular chains along the [001] direction.

Conclusions:

• The crystal structure of C(7)H(7)Cl(2)N(3)OS is stabilized by a combination of π-π interactions, intramolecular Cl⋯N contacts, and extensive intermolecular hydrogen bonding.
• The observed hydrogen bonding patterns, including R(2)(2)(8) and R(2)(1)(7) motifs, play a critical role in the hierarchical self-assembly of molecules into one-dimensional chains.
• The findings provide valuable insights into the structure-property relationships of this class of compounds and contribute to the field of crystal engineering.