{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,4]],"date-time":"2026-04-04T09:43:02Z","timestamp":1775295782184,"version":"3.50.1"},"reference-count":27,"publisher":"International Union of Crystallography (IUCr)","issue":"12","license":[{"start":{"date-parts":[[2016,11,30]],"date-time":"2016-11-30T00:00:00Z","timestamp":1480464000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"},{"start":{"date-parts":[[2016,11,30]],"date-time":"2016-11-30T00:00:00Z","timestamp":1480464000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/2.0\/uk\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"published-print":{"date-parts":[[2016,12,1]]},"abstract":"<jats:p>The title compound, C<jats:sub>5<\/jats:sub>H<jats:sub>4<\/jats:sub>ClNOSe, 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 = 0.012\u2005\u00c5), and its molecular structure is stabilized by an intramolecular secondary Se...O interaction of 2.353\u2005(3)\u2005\u00c5, closing a four-membered N\u2014C\u2014Se...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<jats:italic>ipso<\/jats:italic>-carbon atom. The<jats:italic>endo<\/jats:italic>-cyclic N\u2014C\u2014Se [102.1\u2005(3)\u00b0] and<jats:italic>exo<\/jats:italic>-cyclic C\u2014C\u2014Se [136.9\u2005(3)\u00b0] bond angles deviate significantly from the ideal value of 120\u00b0 for an<jats:italic>sp<\/jats:italic><jats:sup>2<\/jats:sup>-hybridized carbon atom, the former bond angle being much smaller than the latter. In the crystal, molecules are linked by C\u2014H...O hydrogen bonds, forming zigzag chains propagating along [010]. The chains, which stack along the<jats:italic>a-<\/jats:italic>axis direction, are linked by offset \u03c0\u2013\u03c0 interactions [intercentroid distance = 3.960\u2005(3)\u2005\u00c5], forming corrugated sheets parallel to the<jats:italic>ab<\/jats:italic>plane.<\/jats:p>","DOI":"10.1107\/s2056989016018946","type":"journal-article","created":{"date-parts":[[2016,11,30]],"date-time":"2016-11-30T10:34:46Z","timestamp":1480502086000},"page":"1864-1866","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["The synthesis and crystal structure of 2-(chloroselanyl)pyridine 1-oxide: the first monomeric organoselenenyl chloride stabilized by an intramolecular secondary Se...O interaction"],"prefix":"10.1107","volume":"72","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5534-6568","authenticated-orcid":true,"given":"Rizvan K.","family":"Askerov","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhanna V.","family":"Matsulevich","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Galina N.","family":"Borisova","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Svetlana A.","family":"Zalepkina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vasiliy F.","family":"Smirnov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maria M.","family":"Grishina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pavel V.","family":"Dorovatovskii","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander V.","family":"Borisov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Victor N.","family":"Khrustalev","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2016,11,30]]},"reference":[{"key":"su5337_bb1","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1107\/S0907444910048675","volume":"67","author":"Battye","year":"2011","journal-title":"Acta Cryst. 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