Molly A. O’Connor , Anna V. Pavlishchuk , Raymond J. Butcher , Vitaly V. Pavlishchuk , Anthony W. Addison
{"title":"一些硫醚酮及其相关衍生物。","authors":"Molly A. O’Connor , Anna V. Pavlishchuk , Raymond J. Butcher , Vitaly V. Pavlishchuk , Anthony W. Addison","doi":"10.1107/S2056989025004037","DOIUrl":null,"url":null,"abstract":"<div><div>Structures are reported for two thioether-ketones, and for some derived hydrazones, and instances of conformational enantiomerism are delineated. Various types of hydrogen bonds, such as weak C—H⋯S and stronger N—H⋯N and N—H⋯S hydrogen bridges are noted, and intermolecular cases examined <em>via</em> DFT calculations.</div></div><div><div>Structural characteristics are reported for two thioether–ketones, <em><strong>Dtdpe</strong></em> and <em><strong>Mtdp</strong></em> [2-({2-[(2-oxo-2-phenylethyl)sulfanyl]ethyl}sulfanyl)-1-phenylethan-1-one, C<sub>18</sub>H<sub>18</sub>O<sub>2</sub>S<sub>2</sub>, and 2-[(2-oxo-2-phenylethyl)sulfanyl]-1-phenylethan-1-one, C<sub>16</sub>H<sub>14</sub>O<sub>2</sub>S], and for related derivatives, the bis(pyridylhydrazones) <em><strong>Dhpk</strong></em> and <em><strong>Prpsb</strong></em> [2-((2<em>E</em>)-2-{(2<em>Z</em>)-2-phenyl-2-[2-(pyridin-2-yl)hydrazin-1-ylidene]ethylidene}hydrazin-1-yl)pyridine, C<sub>18</sub>H<sub>16</sub>N<sub>6</sub>, and 2-[(2<em>Z</em>,12<em>Z</em>)-3,12-diphenyl-14-(pyridin-2-yl)-5,10-dithia-1,2,13,14-tetraazatetradeca-2,12-dien-1-yl]pyridine, C<sub>30</sub>H<sub>32</sub>N<sub>6</sub>S<sub>2</sub>], as well as for the macrocyclic thiocarbohydrazide derivative <em><strong>Ctrsp</strong></em>[(3<em>E</em>,8<em>Z</em>)-3,9-dimethyl-1,11-dithia-4,5,7,8-tetraazacyclotetradeca-3,8-diene-6-thione, C<sub>10</sub>H<sub>18</sub>N<sub>4</sub>S<sub>3</sub>]. Three of the five compounds exhibit conformational enantiomerism in the solid state. The occurrence of intra- and intermolecular hydrogen bonding is commented upon through quantum mechanical (DFT) calculations. Weak C—H⋯S interactions are noted, while stronger N—H⋯N and N—H⋯S hydrogen bridges are delineated.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 6","pages":"Pages 520-529"},"PeriodicalIF":0.6000,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Some thioether-ketones and their related derivatives\",\"authors\":\"Molly A. O’Connor , Anna V. Pavlishchuk , Raymond J. Butcher , Vitaly V. Pavlishchuk , Anthony W. Addison\",\"doi\":\"10.1107/S2056989025004037\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Structures are reported for two thioether-ketones, and for some derived hydrazones, and instances of conformational enantiomerism are delineated. Various types of hydrogen bonds, such as weak C—H⋯S and stronger N—H⋯N and N—H⋯S hydrogen bridges are noted, and intermolecular cases examined <em>via</em> DFT calculations.</div></div><div><div>Structural characteristics are reported for two thioether–ketones, <em><strong>Dtdpe</strong></em> and <em><strong>Mtdp</strong></em> [2-({2-[(2-oxo-2-phenylethyl)sulfanyl]ethyl}sulfanyl)-1-phenylethan-1-one, C<sub>18</sub>H<sub>18</sub>O<sub>2</sub>S<sub>2</sub>, and 2-[(2-oxo-2-phenylethyl)sulfanyl]-1-phenylethan-1-one, C<sub>16</sub>H<sub>14</sub>O<sub>2</sub>S], and for related derivatives, the bis(pyridylhydrazones) <em><strong>Dhpk</strong></em> and <em><strong>Prpsb</strong></em> [2-((2<em>E</em>)-2-{(2<em>Z</em>)-2-phenyl-2-[2-(pyridin-2-yl)hydrazin-1-ylidene]ethylidene}hydrazin-1-yl)pyridine, C<sub>18</sub>H<sub>16</sub>N<sub>6</sub>, and 2-[(2<em>Z</em>,12<em>Z</em>)-3,12-diphenyl-14-(pyridin-2-yl)-5,10-dithia-1,2,13,14-tetraazatetradeca-2,12-dien-1-yl]pyridine, C<sub>30</sub>H<sub>32</sub>N<sub>6</sub>S<sub>2</sub>], as well as for the macrocyclic thiocarbohydrazide derivative <em><strong>Ctrsp</strong></em>[(3<em>E</em>,8<em>Z</em>)-3,9-dimethyl-1,11-dithia-4,5,7,8-tetraazacyclotetradeca-3,8-diene-6-thione, C<sub>10</sub>H<sub>18</sub>N<sub>4</sub>S<sub>3</sub>]. Three of the five compounds exhibit conformational enantiomerism in the solid state. The occurrence of intra- and intermolecular hydrogen bonding is commented upon through quantum mechanical (DFT) calculations. Weak C—H⋯S interactions are noted, while stronger N—H⋯N and N—H⋯S hydrogen bridges are delineated.</div></div>\",\"PeriodicalId\":7367,\"journal\":{\"name\":\"Acta Crystallographica Section E: Crystallographic Communications\",\"volume\":\"81 6\",\"pages\":\"Pages 520-529\"},\"PeriodicalIF\":0.6000,\"publicationDate\":\"2025-06-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta Crystallographica Section E: Crystallographic Communications\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S2056989025000969\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CRYSTALLOGRAPHY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Crystallographica Section E: Crystallographic Communications","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2056989025000969","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CRYSTALLOGRAPHY","Score":null,"Total":0}
Some thioether-ketones and their related derivatives
Structures are reported for two thioether-ketones, and for some derived hydrazones, and instances of conformational enantiomerism are delineated. Various types of hydrogen bonds, such as weak C—H⋯S and stronger N—H⋯N and N—H⋯S hydrogen bridges are noted, and intermolecular cases examined via DFT calculations.
Structural characteristics are reported for two thioether–ketones, Dtdpe and Mtdp [2-({2-[(2-oxo-2-phenylethyl)sulfanyl]ethyl}sulfanyl)-1-phenylethan-1-one, C18H18O2S2, and 2-[(2-oxo-2-phenylethyl)sulfanyl]-1-phenylethan-1-one, C16H14O2S], and for related derivatives, the bis(pyridylhydrazones) Dhpk and Prpsb [2-((2E)-2-{(2Z)-2-phenyl-2-[2-(pyridin-2-yl)hydrazin-1-ylidene]ethylidene}hydrazin-1-yl)pyridine, C18H16N6, and 2-[(2Z,12Z)-3,12-diphenyl-14-(pyridin-2-yl)-5,10-dithia-1,2,13,14-tetraazatetradeca-2,12-dien-1-yl]pyridine, C30H32N6S2], as well as for the macrocyclic thiocarbohydrazide derivative Ctrsp[(3E,8Z)-3,9-dimethyl-1,11-dithia-4,5,7,8-tetraazacyclotetradeca-3,8-diene-6-thione, C10H18N4S3]. Three of the five compounds exhibit conformational enantiomerism in the solid state. The occurrence of intra- and intermolecular hydrogen bonding is commented upon through quantum mechanical (DFT) calculations. Weak C—H⋯S interactions are noted, while stronger N—H⋯N and N—H⋯S hydrogen bridges are delineated.
期刊介绍:
Acta Crystallographica Section E: Crystallographic Communications is the IUCr''s open-access structural communications journal. It provides a fast, simple and easily accessible publication mechanism for crystal structure determinations of inorganic, metal-organic and organic compounds. The electronic submission, validation, refereeing and publication facilities of the journal ensure rapid and high-quality publication of fully validated structures. The primary article category is Research Communications; these are peer-reviewed articles describing one or more structure determinations with appropriate discussion of the science.