{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,2]],"date-time":"2025-10-02T10:48:39Z","timestamp":1759402119325,"version":"3.33.0"},"reference-count":27,"publisher":"International Union of Crystallography (IUCr)","issue":"9","license":[{"start":{"date-parts":[[2023,8,4]],"date-time":"2023-08-04T00:00:00Z","timestamp":1691107200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2023,8,4]],"date-time":"2023-08-04T00:00:00Z","timestamp":1691107200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"DOI":"10.13039\/100006770","name":"American Chemical Society Petroleum Research Fund","doi-asserted-by":"publisher","award":["56549-UR3"],"award-info":[{"award-number":["56549-UR3"]}],"id":[{"id":"10.13039\/100006770","id-type":"DOI","asserted-by":"publisher"}]}],"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":[[2023,7,27]]},"published-print":{"date-parts":[[2023,9,1]]},"abstract":"<jats:p>The title compound, systematic name 4,4\u2032,6,6\u2032-tetrachloro-2,2\u2032-{[(2-methoxyethyl)azanediyl]bis(methylene)}diphenol (C<jats:sub>17<\/jats:sub>H<jats:sub>17<\/jats:sub>Cl<jats:sub>4<\/jats:sub>NO, <jats:bold>1<\/jats:bold>), was prepared <jats:italic>via<\/jats:italic> a modified Mannich reaction between 2-methoxyethylamine, 2,4-dichlorophenol, and aqueous formaldehyde. The resulting amine bis(phenol) provides an interesting comparison to related species as a result of the electron-withdrawing substituents on the phenol rings, in combination with similar steric parameters. One of the Cl atoms was modeled as a two-component disorder with partial occupancies of 0.49\u2005(3) and 0.51\u2005(3), while the pendant ether group was modeled as a two-component disorder with partial occupancies of 0.867\u2005(3) and 0.133\u2005(3). A comparison of metrical parameters for the title compound and closely related structures provides insight into the use of these species as ligands to support transition-metal complexes for applications as homogeneous catalysts.<\/jats:p>","DOI":"10.1107\/s2056989023006564","type":"journal-article","created":{"date-parts":[[2023,7,31]],"date-time":"2023-07-31T07:10:01Z","timestamp":1690787401000},"page":"782-785","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine"],"prefix":"10.1107","volume":"79","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6856-2796","authenticated-orcid":true,"given":"Bradley M.","family":"Wile","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Claire L.","family":"Griffith","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7407-0533","authenticated-orcid":true,"given":"Adam R.","family":"Johnson","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2023,8,4]]},"reference":[{"key":"zl5047_bb1","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1002\/aoc.3396","volume":"30","author":"Bowser","year":"2016","journal-title":"Appl. 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