(E)-1-[2-(2-Nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]propan-1-one.

Area of Science:

• Crystallography
• Organic Chemistry
• Molecular Structure Analysis

Background:

• Understanding the three-dimensional arrangement of atoms in organic molecules is crucial for predicting their properties and reactivity.
• Aromatic ring systems, such as phenyl and indole, are fundamental building blocks in many biologically active compounds and materials.
• Nitro-benzene moieties are common functional groups that influence electronic properties and intermolecular interactions.

Purpose of the Study:

• To elucidate the precise three-dimensional molecular structure of the title compound, C25H20N2O5S.
• To quantify the spatial relationships (dihedral angles) between the phenyl, indole, and nitro-benzene ring systems.
• To investigate the intermolecular interactions governing crystal packing and molecular assembly.

Main Methods:

• Single-crystal X-ray diffraction was employed to determine the atomic coordinates and bond parameters.
• Dihedral angles between key ring systems were calculated from the crystallographic data.
• Intermolecular interactions, including C-H···O hydrogen bonds and π-π stacking, were analyzed.

Main Results:

• The phenyl ring exhibits significant dihedral angles of 89.88° and 13.98° with the indole and nitro-benzene rings, respectively.
• A near-orthogonal arrangement (88.48°) was observed between the indole and nitro-benzene ring systems.
• A weak intramolecular C-H⋯O interaction contributes to molecular stabilization.
• Intermolecular π-π interactions with centroid-centroid distances of 3.6741(18) and 3.8873(17) Å lead to layered crystal structures parallel to the ab plane.

Conclusions:

• The title compound possesses a distinct, non-planar molecular geometry dictated by the relative orientations of its aromatic components.
• Intramolecular hydrogen bonding and intermolecular π-π stacking are key factors in the solid-state organization of this molecule.
• The detailed structural information provides a foundation for understanding structure-property relationships in related chemical entities.