{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:48:58Z","timestamp":1740174538933,"version":"3.37.3"},"reference-count":21,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2019,9,10]],"date-time":"2019-09-10T00:00:00Z","timestamp":1568073600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2019,9,10]],"date-time":"2019-09-10T00:00:00Z","timestamp":1568073600000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"National Research Fund Thuthuka","award":["99164"],"award-info":[{"award-number":["99164"]}]},{"DOI":"10.13039\/501100006565","name":"University of Johannesburg","doi-asserted-by":"crossref","award":["UJ\u2013GES post-doctoral fellowship"],"award-info":[{"award-number":["UJ\u2013GES post-doctoral fellowship"]}],"id":[{"id":"10.13039\/501100006565","id-type":"DOI","asserted-by":"crossref"}]}],"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"],"accepted":{"date-parts":[[2019,9,9]]},"published-print":{"date-parts":[[2019,10,1]]},"abstract":"<jats:p>The title compound, C<jats:sub>10<\/jats:sub>H<jats:sub>13<\/jats:sub>Cl<jats:sub>2<\/jats:sub>NO<jats:sub>2<\/jats:sub>\u00b7C<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>Cl<jats:sub>2<\/jats:sub>O, was formed from the incomplete Mannich condensation reaction of 3-aminopropan-1-ol, formaldehyde and 2,4-dichlorophenol in methanol. This resulted in the formation of a co-crystal of the zwitterionic Mannich base, 2,4-dichloro-6-{[(3-hydroxypropyl)azaniumyl]methyl}phenolate and the unreacted 2,4-dichlorophenol. The compound crystallizes in the monoclinic crystal system (in space group <jats:italic>Cc<\/jats:italic>) and the asymmetric unit contains a molecule each of the 2,4-dichlorophenol and 2,4-dichloro-6-{[(3-hydroxypropyl)azaniumyl]methyl}phenolate. Examination of the crystal structure shows that the two components are clearly linked together by hydrogen bonds. The packing patterns are most interesting along the <jats:italic>b<\/jats:italic> and the <jats:italic>c<\/jats:italic> axes, where the co-crystal in the unit cell packs in a manner that shows alternating aromatic dichlorophenol fragments and polar hydrogen-bonded channels. The 2,4-dichlorophenol rings stack on top of one another, and these are held together by \u03c0\u2013\u03c0 interactions. The crystal studied was refined as an inversion twin.<\/jats:p>","DOI":"10.1107\/s2056989019012544","type":"journal-article","created":{"date-parts":[[2019,9,10]],"date-time":"2019-09-10T09:20:46Z","timestamp":1568107246000},"page":"1452-1455","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["The crystal structure of the zwitterionic co-crystal of 2,4-dichloro-6-{[(3-hydroxypropyl)azaniumyl]methyl}phenolate and 2,4-dichlorophenol"],"prefix":"10.1107","volume":"75","author":[{"given":"Bhawna","family":"Uprety","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6617-1011","authenticated-orcid":true,"given":"Charmaine","family":"Arderne","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2019,9,10]]},"reference":[{"key":"fy2140_bb1","first-page":"847","volume":"8","author":"Bavoux","year":"1979","journal-title":"Cryst. Struct. Commun."},{"key":"fy2140_bb2","unstructured":"Bruker (2014). APEX2. Bruker AXS, Inc., Madison, Wisconsin, USA."},{"key":"fy2140_bb3","unstructured":"Bruker (2016). SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA."},{"key":"fy2140_bb4","doi-asserted-by":"crossref","first-page":"2133","DOI":"10.1021\/ci049780b","volume":"44","author":"Bruno","year":"2004","journal-title":"J. Chem. Inf. Comput. Sci."},{"key":"fy2140_bb5","doi-asserted-by":"crossref","first-page":"1688","DOI":"10.1002\/cbic.200700182","volume":"8","author":"B\u00fcttner","year":"2007","journal-title":"ChemBioChem"},{"key":"fy2140_bb6","doi-asserted-by":"crossref","first-page":"6549","DOI":"10.1021\/ja00017a028","volume":"113","author":"Byrn","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"fy2140_bb7","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1107\/S2053229613033810","volume":"70","author":"Cai","year":"2014","journal-title":"Acta Cryst. C"},{"key":"fy2140_bb8","doi-asserted-by":"crossref","first-page":"720","DOI":"10.1107\/S2053229616013577","volume":"72","author":"Cai","year":"2016","journal-title":"Acta Cryst. C"},{"key":"fy2140_bb9","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"fy2140_bb10","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"fy2140_bb11","doi-asserted-by":"crossref","first-page":"2874","DOI":"10.1021\/om100103u","volume":"29","author":"Lee","year":"2010","journal-title":"Organometallics"},{"key":"fy2140_bb12","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1107\/S0021889807067908","volume":"41","author":"Macrae","year":"2008","journal-title":"J. Appl. Cryst."},{"key":"fy2140_bb13","doi-asserted-by":"crossref","first-page":"17736","DOI":"10.1039\/C5DT02716K","volume":"44","author":"Maurya","year":"2015","journal-title":"Dalton Trans."},{"key":"fy2140_bb14","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1134\/S0036023610020117","volume":"55","author":"Pestov","year":"2010","journal-title":"Russ. J. Inorg. Chem."},{"key":"fy2140_bb15","doi-asserted-by":"crossref","first-page":"1048","DOI":"10.1002\/ejic.201101103","author":"Riisi\u00f6","year":"2012","journal-title":"Eur. J. Inorg. Chem."},{"key":"fy2140_bb16","doi-asserted-by":"crossref","first-page":"8591","DOI":"10.1021\/ic400663y","volume":"52","author":"Riisi\u00f6","year":"2013","journal-title":"Inorg. Chem."},{"key":"fy2140_bb17","doi-asserted-by":"crossref","first-page":"987","DOI":"10.1080\/00397910500501243","volume":"36","author":"Sarhan","year":"2006","journal-title":"Synth. Commun."},{"key":"fy2140_bb18","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"fy2140_bb19","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"fy2140_bb20","doi-asserted-by":"crossref","first-page":"1223","DOI":"10.1016\/j.poly.2005.08.044","volume":"25","author":"Sopo","year":"2006","journal-title":"Polyhedron"},{"key":"fy2140_bb21","doi-asserted-by":"crossref","first-page":"148","DOI":"10.1107\/S090744490804362X","volume":"65","author":"Spek","year":"2009","journal-title":"Acta Cryst. D"}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2019\/10\/00\/fy2140\/fy2140.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/journals.iucr.org\/e\/issues\/2019\/10\/00\/fy2140\/fy2140.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T11:08:34Z","timestamp":1736766514000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989019012544"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,9,10]]},"references-count":21,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2019,10]]}},"alternative-id":["S2056989019012544"],"URL":"https:\/\/doi.org\/10.1107\/s2056989019012544","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989019012544\/fy2140sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989019012544\/fy2140Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989019012544\/fy2140Isup3.mol","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"type":"electronic","value":"2056-9890"}],"subject":[],"published":{"date-parts":[[2019,9,10]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"http:\/\/journals.iucr.org\/e"},"group":{"name":"general","label":"General"}},{"value":"research communications","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?fy2140","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"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":"10 June 2019","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"9 September 2019","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"10 September 2019","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":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?fy2140"}},{"value":"\u00a9 2019 Uprety and Arderne","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}},{"value":"Creative Commons Attribution (CC-BY)","order":1,"name":"license","label":"Licence","explanation":{"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}