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Updated: May 27, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
(E)-N'-(3-Bromo-5-chloro-2-hy-droxy-benzyl-idene)nicotinohydrazide.
This study details the crystal structure of a novel compound, C(13)H(9)BrClN(3)O(2), revealing distinct molecular arrangements and hydrogen bonding interactions critical for its stability.
Area of Science:
- Crystallography
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Understanding molecular interactions is key in crystal engineering.
- The title compound, C(13)H(9)BrClN(3)O(2), presents a unique structural framework.
- Previous studies on similar heterocyclic compounds inform the current investigation.
Purpose of the Study:
- To elucidate the crystal structure of C(13)H(9)BrClN(3)O(2).
- To analyze the intermolecular and intramolecular interactions governing crystal packing.
- To characterize the dihedral angles and configurations within the molecule.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
- Analysis of hydrogen bonding networks, including graph-set motifs.
- Investigation of non-covalent interactions such as π-π stacking.
Main Results:
- Two independent molecules of C(13)H(9)BrClN(3)O(2) were identified in the asymmetric unit.
- Dihedral angles between benzene and pyridine rings were measured at 8.23(9)° and 52.84(12)°.
- Both molecules adopt an E configuration, stabilized by intra- and intermolecular hydrogen bonds (C-H⋯O, O-H⋯N, N-H⋯O, N-H⋯N) and π-π interactions.
Conclusions:
- The crystal structure reveals specific conformational preferences and hydrogen bonding patterns.
- The identified interactions, including π-π stacking, significantly contribute to the overall crystal stability.
- This detailed structural analysis provides a foundation for understanding the properties and potential applications of this compound.
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