The synthesis and crystal structure of 2-(chloroselanyl)pyridine 1-oxide: The first monomeric organoselenenyl chloride stabilized by an intramolecular secondary Se⋯O interaction

The title compound, C5H4ClNOSe, is the product of the reaction of sulfuryl chloride and 2-selanyl-1-pyridine 1-oxide in dichloromethane. The molecule has an almost planar geometry (r.m.s. deviation = 0.012Å), and its molecular structure is stabilized by an intramolecular secondary Se⋯O interaction of 2.353(3)Å, closing a four-membered N - C - Se⋯O ring. The title compound represents the first monomeric organoselenenyl chloride stabilized intramolecularly by an interaction of this type. The non-valent attractive Se⋯O interaction results in a substantial distortion of the geometry of the ipso-carbon atom. The endo-cyclic N - C - Se [102.1(3)°] and exo-cyclic C - C - Se [136.9(3)°] bond angles deviate significantly from the ideal value of 120° for an sp 2-hybridized carbon atom, the former bond angle being much smaller than the latter. In the crystal, molecules are linked by C - H⋯O hydrogen bonds, forming zigzag chains propagating along [010]. The chains, which stack along the a-axis direction, are linked by offset π-π interactions [intercentroid distance = 3.960(3)Å], forming corrugated sheets parallel to the ab plane.

Askerov R.K.1 , Matsulevich Z.V.2 , Borisova G.N.2 , Zalepkina S.A.3 , Smirnov V.F.3 , Grishina M.M. 4 , Dorovatovskii P.V.5 , Borisov A.V.2 , Khrustalev V.N. 4, 6
International Union of Crystallography
  • 1 Department of Chemistry, Baku State University, 23 Z. Khalilov St., Baku, AZ-1148, Azerbaijan
  • 2 R.E. Alekseev Nizhny Novgorod State Technical University, 24 Minin St., Nizhny Novgorod, 603950, Russian Federation
  • 3 N.I. Lobachevsky State University of Nizhny Novgorod, 23 Gagarin Prosp., Nizhny Novgorod, 603950, Russian Federation
  • 4 Inorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St., Moscow, 117198, Russian Federation
  • 5 National Research Center, Kurchatov Institute, 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation
  • 6 X-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., B-334, Moscow, 119991, Russian Federation
Ключевые слова
crystal structure; intramolecular stabilization; organoselenenyl chloride; secondary interactions; synchrotron radiation
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