Syntheses, crystal structures, Hirshfeld surface analyses and crystal voids of 1-(4-bromophenyl)-2,2-dichloroethan-1-one and 2,2-dibromo-1-(p-tolyl)ethan-1-one

Syntheses, crystal structures, Hirshfeld surface analyses and crystal voids of 1-(4-bromophenyl)-2,2-dichloroethan-1-one and 2,2-dibromo-1-(p-tolyl)ethan-1-one Full article

Journal

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

Output data

Year: 2025, Volume: 81, Number: 2, Pages: 120-126 Pages count : 7 DOI: 10.1107/s205698902500012x

Authors

Gurbanov Atash V. ^1,2 , Guseinov Firudin I. ^3,4 , Samigullina Aida I. ⁴ , Hökelek Tuncer ⁵ , Hasanov Khudayar I. ⁶ , Javadzade Tahir A. ⁷ , Belay Alebel N. ⁸

Affiliations

1	Centro de Quimica Estrutural, Instituto Superior Tecnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisbon, Portugal
2	Excellence Center, Baku State University, Z. Xalilov Str. 23, AZ 1148 Baku, Azerbaijan
3	Kosygin State University of Russia, 117997 Moscow, Russian Federation
4	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
5	Hacettepe University, Department of Physics, 06800 Beytepe-Ankara, Türkiye
6	Azerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade Str. 14, AZ 1022 Baku, Azerbaijan
7	Department of Chemistry and Chemical Engineering, Khazar University, Mahzati Str. 41, AZ 1096 Baku, Azerbaijan
8	Department of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, Ethiopia

The asymmetric units of the compounds, C8H5BrCl2O (I), and C9H8Br2O (II), contain two and one crystallographically independent molecules, respectively. In compound (I), the planar rings are oriented at a dihedral angle of 13.23 (8)°. In crystals of both compounds, intermolecular C—H⋯O hydrogen bonds link the molecules into infinite chains along the b-axis direction. In crystal of (I), there are π–π interactions between the centroids of the parallel rings with centroid-to-centroid distances of 3.5974 (14), 3.6178 (16) and 3.9387 (16) Å while neither π–π nor C—H⋯ π(ring) interactions are present in (II). The Hirshfeld surface analyses of the crystal structures indicate that the most important contributions for the crystal packings are from H⋯Cl/Cl⋯H (27.5%), H⋯O/O⋯H (15.0%), H⋯Br/Br⋯H (10.2%) and H⋯H (9.0%) for (I) and H⋯Br/Br⋯H (36.1%), H⋯H (22.2%), H⋯O/O⋯H (14.1%) and H⋯C/C⋯H (13.9%) for (II). Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packings. The volumes of the crystal voids and the percentages of free spaces in the unit cells were calculated to 111.55 Å3 and 12.27% for (I) and 63.37 Å and 6.69% for (II), showing that no large cavities are present in either structure.

Gurbanov A.V. , Guseinov F.I. , Samigullina A.I. , Hökelek T. , Hasanov K.I. , Javadzade T.A. , Belay A.N.
Syntheses, crystal structures, Hirshfeld surface analyses and crystal voids of 1-(4-bromophenyl)-2,2-dichloroethan-1-one and 2,2-dibromo-1-(p-tolyl)ethan-1-one
Acta Crystallographica Section E: Crystallographic Communications. 2025. V.81. N2. P.120-126. DOI: 10.1107/s205698902500012x OpenAlex

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