{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T05:13:43Z","timestamp":1736831623993,"version":"3.33.0"},"reference-count":0,"publisher":"International Union of Crystallography (IUCr)","issue":"9","license":[{"start":{"date-parts":[[2014,8,23]],"date-time":"2014-08-23T00:00:00Z","timestamp":1408752000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2014,8,23]],"date-time":"2014-08-23T00:00:00Z","timestamp":1408752000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"published-print":{"date-parts":[[2014,9,1]]},"abstract":"<jats:p>The structures of four halogenated<jats:italic>N<\/jats:italic>,2-diarylacetamides are reported and compared with a range of analogues.<jats:italic>N<\/jats:italic>-(4-Chloro-3-methylphenyl)-2-phenylacetamide, C<jats:sub>15<\/jats:sub>H<jats:sub>14<\/jats:sub>ClNO, (I), and<jats:italic>N<\/jats:italic>-(4-bromo-3-methylphenyl)-2-phenylacetamide, C<jats:sub>15<\/jats:sub>H<jats:sub>14<\/jats:sub>BrNO, (II), are isostructural in the space group<jats:italic>P<\/jats:italic>\\overline{1}. The molecules of (I) and (II) are linked into chains of rings by a combination of N\u2014H...O and C\u2014H...\u03c0(arene) hydrogen bonds. The molecules of<jats:italic>N<\/jats:italic>-(4-chloro-3-methylphenyl)-2-(2,4-dichlorophenyl)acetamide, C<jats:sub>15<\/jats:sub>H<jats:sub>12<\/jats:sub>Cl<jats:sub>3<\/jats:sub>NO, (III), and<jats:italic>N<\/jats:italic>-(4-bromo-3-methylphenyl)-2-(2-chlorophenyl)acetamide, C<jats:sub>15<\/jats:sub>H<jats:sub>13<\/jats:sub>BrClNO, (IV), are linked into simple<jats:italic>C<\/jats:italic>(4) chains by N\u2014H...O hydrogen bonds, but significant C\u2014H...\u03c0(arene) interactions are absent. The<jats:italic>N<\/jats:italic>-aryl groups in compounds (III) and (IV) adopt a different orientation, by<jats:italic>ca<\/jats:italic>180\u00b0, from that of the corresponding groups in compounds (I) and (II), but otherwise the conformations of (I)\u2013(IV) are very similar. Comparisons are drawn between compounds (I) and (IV) and a range of analogues of the type<jats:italic>R<\/jats:italic><jats:sup>1<\/jats:sup>CH<jats:sub>2<\/jats:sub>CONH<jats:italic>R<\/jats:italic><jats:sup>2<\/jats:sup>, where<jats:italic>R<\/jats:italic><jats:sup>2<\/jats:sup>represents a halogenated aryl ring and<jats:italic>R<\/jats:italic><jats:sup>1<\/jats:sup>represents either another halogenated aryl ring or a naphthalen-1-yl unit.<\/jats:p>","DOI":"10.1107\/s2053229614018713","type":"journal-article","created":{"date-parts":[[2014,10,30]],"date-time":"2014-10-30T13:23:53Z","timestamp":1414675433000},"page":"889-894","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":5,"title":["Halogenated<i>C<\/i>,<i>N<\/i>-diarylacetamides: molecular conformations and supramolecular assembly"],"prefix":"10.1107","volume":"70","author":[{"given":"Prakash S.","family":"Nayak","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jerry P.","family":"Jasinski","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"James A.","family":"Golen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Badiadka","family":"Narayana","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Manpreet","family":"Kaur","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hemmige S.","family":"Yathirajan","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christopher","family":"Glidewell","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2014,8,23]]},"container-title":["Acta Crystallographica Section C Structural Chemistry"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2014\/09\/00\/sk3561\/sk3561.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2014\/09\/00\/sk3561\/sk3561.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T09:59:00Z","timestamp":1736762340000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2053229614018713"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,8,23]]},"references-count":0,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2014,9]]}},"alternative-id":["S2053229614018713"],"URL":"https:\/\/doi.org\/10.1107\/s2053229614018713","relation":{},"ISSN":["2053-2296"],"issn-type":[{"type":"electronic","value":"2053-2296"}],"subject":[],"published":{"date-parts":[[2014,8,23]]},"assertion":[{"value":"Acta Crystallographica Section C: Structural Chemistry","name":"journal","label":"Journal","explanation":{"URL":"http:\/\/journals.iucr.org\/c"}},{"value":"research papers","name":"content_type","label":"Content type","explanation":{"URL":"http:\/\/journals.iucr.org\/c\/issues\/2011\/01\/00\/me0438\/index.html"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"18 August 2014","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"18 August 2014","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"23 August 2014","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"http:\/\/scripts.iucr.org\/cgi-bin\/sendsup?sk3561"}},{"value":"\u00a9 2014 International Union of Crystallography","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licensing","label":"Copyright and licencing"}}]}}