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

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 Full article

Journal

Acta Crystallographica Section E: Crystallographic Communications
ISSN: 2056-9890

Output data

Year: 2025, Volume: 81, Number: 6, Pages: 538-542 Pages count : 5 DOI: 10.1107/s2056989025004359

Authors

Guseinov Firudin I ^1,2 , Hökelek Tuncer ³ , Afanaseva Ksenia A ^1,2 , Shuvalova Elena V ² , Glukhov Lev M ² , Samigullina Aida I ² , Belay Alebel N ⁴

Affiliations

1	Kosygin State University of Russia, 117997 Moscow, Russian Federation.
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation.
3	Hacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye.
4	Department of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia.

The title compounds, C10H9Cl2FN2O3, (I), and C11H12Cl2N2O3, (II), are α,α-dihalo-β-diketone urea derivatives, which contain 4-fluorophenyl and p-tolyl groups, respectively. The conformation about the CO—CCl2—CO—Nu (O = keto, Cl2 = dichloro, u = urea) bond is anti in (I) and gauche in (II). 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).

Guseinov F.I. , Hökelek T. , Afanaseva K.A. , Shuvalova E.V. , Glukhov L.M. , Samigullina A.I. , Belay A.N.
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
Acta Crystallographica Section E: Crystallographic Communications. 2025. V.81. N6. P.538-542. DOI: 10.1107/s2056989025004359 WOS Scopus OpenAlex

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