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Crystal structure of 1-{2-[(2-meth-oxy-phen-yl)selan-yl]phen-yl}-4-phenyl-1H-1,2,3-triazole.

ABSTRACT: In the title compound, C21H17N3OSe, the dihedral angles between the central five-membered ring and the C- and N-bound rings are 17.89?(10) and 42.35?(10)°, respectively, indicating the mol-ecule is twisted. The dihedral angle between the Se-bound rings is 85.36?(10)°. A close intra-molecular Se?O contact of 2.8507?(13)?Å is noted. In the crystal, C-H?O, C-H?N and C-H?? inter-actions lead to the formation of supra-molecular layers parallel to (011); these stack with no specific inter-molecular inter-actions between them.

SUBMITTER: Camargo LR

PROVIDER: S-EPMC4350762 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Crystal structure of 1-{2-[(2-meth-oxy-phen-yl)selan-yl]phen-yl}-4-phenyl-1H-1,2,3-triazole.

Camargo Leandro R S LR Zukerman-Schpector Julio J Deobald Anna M AM Braga Antonio L AL Tiekink Edward R T ER

Acta crystallographica. Section E, Crystallographic communications 20150225 Pt 3

In the title compound, C21H17N3OSe, the dihedral angles between the central five-membered ring and the C- and N-bound rings are 17.89 (10) and 42.35 (10)°, respectively, indicating the mol-ecule is twisted. The dihedral angle between the Se-bound rings is 85.36 (10)°. A close intra-molecular Se⋯O contact of 2.8507 (13) Å is noted. In the crystal, C-H⋯O, C-H⋯N and C-H⋯π inter-actions lead to the formation of supra-molecular layers parallel to (011); these stack with no specific inter-molecular in ...[more]

PMID: 25844249

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Project description:The title compound, C19H17ClN4O2, was obtained via a two-step synthesis involving the enol-mediated click Dimroth reaction of 4-azido-anisole with methyl 3-cyclo-propyl-3-oxo-propano-ate leading to the 5-cyclo-propyl-1-(4-meth-oxy-phen-yl)-1H-1,2,3-triazole-4-carb-oxy-lic acid and subsequent acid amidation with 4-chloro-aniline by 1,1'-carbonyl-diimidazole (CDI). It crystallizes in space group P21/n, with one mol-ecule in the asymmetric unit. In the extended structure, two mol-ecules arranged in a near coplanar fashion relative to the triazole ring planes are inter-connected by N-H?N and C-H?N hydrogen bonds into a homodimer. The formation of dimers is a consequence of the above inter-action and the edge-to-face stacking of aromatic rings, which are turned by 58.0?(3)° relative to each other. The dimers are linked by C-H?O inter-actions into ribbons. DFT calculations demonstrate that the frontier mol-ecular orbitals are well separated in energy and the HOMO is largely localized on the 4-chloro-phenyl amide motif while the LUMO is associated with aryl-triazole grouping. A Hirshfeld surface analysis was performed to further analyse the inter-molecular inter-actions.

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