Synthesis, crystal structure and Hirshfeld surface analysis of 1-[(1-benzyl-1 H -1,2,3-triazol-4-yl)methyl]-3-(2-oxo-2-phenylethyl)-1,3-dihydro-2 H -benzimidazol-2-one

In plain language

Structural analysis reveals the precise three-dimensional molecular configuration of a synthesised organic compound containing triazole and benzimidazolone components. Within the molecule, both the benzyltriazole portion and the phenyl section display structural disorder across two distinct sites. In the solid state, molecules organise into layers parallel to the crystallographic plane, held together by weak carbon-hydrogen to oxygen and carbon-hydrogen to nitrogen bonds, alongside interactions between hydrogen atoms and aromatic rings. These non-covalent links generate specific closed-ring motifs within the lattice network. Quantitative Hirshfeld surface analysis demonstrates that the structural cohesion of the crystal packing is driven predominantly by hydrogen-hydrogen contacts, which account for over forty per cent of all intermolecular interactions. Contacts between hydrogen and carbon atoms form the second largest contribution, followed by smaller contributions involving oxygen and nitrogen atoms.

Key takeaways

The compound exhibits structural disorder across two sites within its benzyltriazole and phenyl groups.
Molecules form planar layers stabilised by carbon-hydrogen interactions with oxygen, nitrogen, and aromatic rings.
Hydrogen-bonding arrangements generate distinct ten-membered and sixteen-membered ring motifs in the crystal lattice.
Hirshfeld surface analysis identifies hydrogen-hydrogen interactions as the dominant packing contribution at 41.3 per cent.
Hydrogen-carbon contacts contribute 31.1 per cent of interactions, with oxygen and nitrogen contacts providing the remainder.

Why it matters

Determining the precise geometry and intermolecular forces of complex heterocyclic molecules provides fundamental insights into solid-state chemistry. Understanding how such structures assemble through hydrogen bonding and surface contacts helps chemists comprehend molecular stability and packing behaviour, supporting future research in organic synthesis and molecular design.

Commercialisation angle

The abstract does not indicate an application pathway.

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Abstract

In the title molecule, C 25 H 21 N 5 O 2 , the benzyltriazole moiety and the phenyl portion of the 3-(2-oxo-2-phenylethyl) group are disordered over two sets of sites. In the crystal, layers of molecules parallel to the ab plane are generated by C—H...O and C—H...N hydrogen bonds, enclosing R 2 2 (10) and R 2 2 (16) ring motifs, and C—H...π(ring) interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (41.3%), H...C/C...H (31.1%), H...O/O...H (13.2%) and H...N/N...H (10.7%) interactions.

Research topics

Crystal structures of chemical compounds
Synthesis and Reactivity of Heterocycles
Crystallography and molecular interactions

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