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
The title compounds, C<sub>10</sub>H<sub>9</sub>Cl<sub>2</sub>FN<sub>2</sub>O<sub>3</sub>, (<b>I</b>), and C<sub>11</sub>H<sub>12</sub>Cl<sub>2</sub>N<sub>2</sub>O<sub>3</sub>, (<b>II</b>), are α,α-dihalo-β-diketone urea derivatives, which contain 4-fluoro-phenyl and <i>p</i>-tolyl groups, respectively. The conformation about the C<sub>O</sub>-C<sub>Cl2</sub>-C<sub>O</sub>-N<sub>u</sub> (O = keto, Cl2 = di-chloro, u = urea) bond is <i>anti</i> in (<b>I</b>) and <i>gauche</i> in (<b>II</b>). In the crystals of both compounds, O-H⋯O hydrogen bonds generate inversion dimers and the dimers are linked into (100) layers by N-H⋯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).
Authors
- L. М. Glukhov (ORCID: https://orcid.org/0000-0003-1906-9000)
- Aida I. Samigullina (ORCID: https://orcid.org/0000-0002-6791-9973)
- Alebel N. Belay (ORCID: https://orcid.org/0000-0003-4175-5656)
- Tuncer Hökelek (ORCID: https://orcid.org/0000-0002-8602-4382)
- Е. В. Шувалова (ORCID: https://orcid.org/0000-0002-3163-5207)
- Firudin I. Guseinov (ORCID: https://orcid.org/0000-0002-6769-0232)
- Ksenia A. Afanaseva
Institutions
- A. N. Kosygin Moscow State Textile University (RU)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
- Bahir Dar University (ET)
- Hacettepe University (TR)
Publication Details
- Journal
- Acta Crystallographica Section E Crystallographic Communications
- Published
- 2025-05-15
- DOI
- https://doi.org/10.1107/s2056989025004359
- Citations
- 1
- Primary Topic
- Crystal structures of chemical compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.54