{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,6,6]],"date-time":"2025-06-06T08:10:06Z","timestamp":1749197406274,"version":"3.41.0"},"reference-count":15,"publisher":"International Union of Crystallography (IUCr)","issue":"6","license":[{"start":{"date-parts":[[2025,5,20]],"date-time":"2025-05-20T00:00:00Z","timestamp":1747699200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,5,20]],"date-time":"2025-05-20T00:00:00Z","timestamp":1747699200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/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"],"accepted":{"date-parts":[[2025,5,14]]},"published-print":{"date-parts":[[2025,6,1]]},"abstract":"<jats:p>The title compounds, C<jats:sub>10<\/jats:sub>H<jats:sub>9<\/jats:sub>Cl<jats:sub>2<\/jats:sub>FN<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>, (<jats:bold>I<\/jats:bold>), and C<jats:sub>11<\/jats:sub>H<jats:sub>12<\/jats:sub>Cl<jats:sub>2<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>, (<jats:bold>II<\/jats:bold>), are \u03b1,\u03b1-dihalo-\u03b2-diketone urea derivatives, which contain 4-fluorophenyl and <jats:italic>p<\/jats:italic>-tolyl groups, respectively. The conformation about the C<jats:sub>O<\/jats:sub>\u2014C<jats:sub>Cl2<\/jats:sub>\u2014C<jats:sub>O<\/jats:sub>\u2014N<jats:sub>u<\/jats:sub> (O = keto, Cl2 = dichloro, u = urea) bond is <jats:italic>anti<\/jats:italic> in (<jats:bold>I<\/jats:bold>) and <jats:italic>gauche<\/jats:italic> in (<jats:bold>II<\/jats:bold>). In the crystals of both compounds, O\u2014H...O hydrogen bonds generate inversion dimers and the dimers are linked into (100) layers by N\u2014H...O hydrogen bonds. The Hirshfeld surface analyses of the crystal structures indicate that the most important contributions for the crystal packings are from H...O\/O...H (22.3%), H...H (20.9%), H...Cl\/Cl...H (15.6%) and H...C\/C...H (10.3%) for (I) and H...H (31.7%), H...O\/O...H (25.1%), H...Cl\/Cl...H (21.1%) and H...C\/C...H (9.5%) for (II).<\/jats:p>","DOI":"10.1107\/s2056989025004359","type":"journal-article","created":{"date-parts":[[2025,5,15]],"date-time":"2025-05-15T14:46:22Z","timestamp":1747320382000},"page":"538-542","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Syntheses and structures of 1-[2,2-dichloro-1-hydroxy-3-(4-methylphenyl)-3-oxopropyl]urea and 1-[2,2-dichloro-3-(4-fluorophenyl)-1-hydroxy-3-oxopropyl]urea"],"prefix":"10.1107","volume":"81","author":[{"given":"Firudin I.","family":"Guseinov","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8602-4382","authenticated-orcid":true,"given":"Tuncer","family":"H\u00f6kelek","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ksenia A.","family":"Afanaseva","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Elena V.","family":"Shuvalova","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lev M.","family":"Glukhov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6791-9973","authenticated-orcid":true,"given":"Aida I.","family":"Samigullina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4175-5656","authenticated-orcid":true,"given":"Alebel N.","family":"Belay","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2025,5,20]]},"reference":[{"key":"hb8127_bb1","doi-asserted-by":"crossref","first-page":"116955","DOI":"10.1016\/j.poly.2024.116955","volume":"255","author":"Aliyeva","year":"2024","journal-title":"Polyhedron"},{"key":"hb8127_bb2","doi-asserted-by":"crossref","first-page":"107","DOI":"10.21285\/2227-2925-2020-10-1-107-113","volume":"10","author":"Aliyev","year":"2020","journal-title":"Izvest. 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