title: The synthesis and crystal structure of 2-(chloro-selan-yl)pyridine 1-oxide: the first monomeric organoselenenyl chloride stabilized by an intra-molecular secondary Se⋯O inter-action.
abstract: The title compound, C5H4ClNOSe, is the product of the reaction of sulfuryl chloride and 2-selanyl-1-pyridine 1-oxide in di-chloro-methane. The mol-ecule has an almost planar geometry (r.m.s. deviation = 0.012 Å), and its mol-ecular structure is stabilized by an intra-molecular secondary Se⋯O inter-action of 2.353 (3) Å, closing a four-membered N-C-Se⋯O ring. The title compound represents the first monomeric organoselenenyl chloride stabilized intra-molecularly by an inter-action of this type. The non-valent attractive Se⋯O inter-action results in a substantial distortion of the geometry of theipso-carbon atom. Theendo-cyclic N-C-Se [102.1 (3)°] andexo-cyclic C-C-Se [136.9 (3)°] bond angles deviate significantly from the ideal value of 120° for ansp2-hybridized carbon atom, the former bond angle being much smaller than the latter. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming zigzag chains propagating along [010]. The chains, which stack along thea-axis direction, are linked by offset π-π inter-actions [inter-centroid distance = 3.960 (3) Å], forming corrugated sheets parallel to theabplane.
authors.affiliation: Department of Chemistry, Baku State University, 23 Z. Khalilov St., Baku, AZ-1148, Azerbaijan.
authors.forename: Rizvan K
authors.initials: RK
authors.lastname: Askerov
authors.affiliation: R.E. Alekseev Nizhny Novgorod State Technical University, 24 Minin St., Nizhny Novgorod, 603950, Russian Federation.
authors.forename: Zhanna V
authors.initials: ZV
authors.lastname: Matsulevich
authors.affiliation: R.E. Alekseev Nizhny Novgorod State Technical University, 24 Minin St., Nizhny Novgorod, 603950, Russian Federation.
authors.forename: Galina N
authors.initials: GN
authors.lastname: Borisova
authors.affiliation: N.I. Lobachevsky State University of Nizhny Novgorod, 23 Gagarin Prosp., Nizhny Novgorod, 603950, Russian Federation.
authors.forename: Svetlana A
authors.initials: SA
authors.lastname: Zalepkina
authors.affiliation: N.I. Lobachevsky State University of Nizhny Novgorod, 23 Gagarin Prosp., Nizhny Novgorod, 603950, Russian Federation.
authors.forename: Vasiliy F
authors.initials: VF
authors.lastname: Smirnov
authors.affiliation: Inorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St., Moscow, 117198, Russian Federation.
authors.forename: Maria M
authors.initials: MM
authors.lastname: Grishina
authors.affiliation: National Research Center "Kurchatov Institute", 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation.
authors.forename: Pavel V
authors.initials: PV
authors.lastname: Dorovatovskii
authors.affiliation: R.E. Alekseev Nizhny Novgorod State Technical University, 24 Minin St., Nizhny Novgorod, 603950, Russian Federation.
authors.forename: Alexander V
authors.initials: AV
authors.lastname: Borisov
authors.affiliation: Inorganic Chemistry Department, Peoples' Friendship University of Russia, 6 Miklukho-Maklay St., Moscow, 117198, Russian Federation; X-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St., B-334, Moscow 119991, Russian Federation.
authors.forename: Victor N
authors.initials: VN
authors.lastname: Khrustalev
keywords: crystal structure; intra­molecular stabilization; organoselenenyl chloride; secondary inter­actions; synchrotron radiation