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
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 bon...
Saved in:
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2025-02-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | https://journals.iucr.org/paper?S205698902500012X |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832087002459144192 |
|---|---|
| author | Atash V. Gurbanov Firudin I. Guseinov Aida I. Samigullina Tuncer Hökelek Khudayar I. Hasanov Tahir A. Javadzade Alebel N. Belay |
| author_facet | Atash V. Gurbanov Firudin I. Guseinov Aida I. Samigullina Tuncer Hökelek Khudayar I. Hasanov Tahir A. Javadzade Alebel N. Belay |
| author_sort | Atash V. Gurbanov |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-1b2be23476fd4b83b9238d8d4f34d1bb |
| institution | Kabale University |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-1b2be23476fd4b83b9238d8d4f34d1bb2025-02-06T07:27:16ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-02-0181212012610.1107/S205698902500012Xnx2018Syntheses, 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-oneAtash V. Gurbanov0Firudin I. Guseinov1Aida I. Samigullina2Tuncer Hökelek3Khudayar I. Hasanov4Tahir A. Javadzade5Alebel N. Belay6Excellence Center, Baku State University, Z. Xalilov Str. 23, AZ 1148 Baku, AzerbaijanKosygin State University of Russia, 117997 Moscow, Russian FederationN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian FederationHacettepe University, Department of Physics, 06800 Beytepe-Ankara, TürkiyeAzerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade Str. 14, AZ 1022 Baku, AzerbaijanDepartment of Chemistry and Chemical Engineering, Khazar University, Mahzati Str. 41, AZ 1096 Baku, AzerbaijanDepartment of Chemistry, Bahir Dar University, PO Box 79, Bahir Dar, EthiopiaThe 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.https://journals.iucr.org/paper?S205698902500012Xcrystal structurenon-covalent interactionshydrogen bond |
| spellingShingle | Atash V. Gurbanov Firudin I. Guseinov Aida I. Samigullina Tuncer Hökelek Khudayar I. Hasanov Tahir A. Javadzade Alebel N. Belay 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 crystal structure non-covalent interactions hydrogen bond |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | crystal structure non-covalent interactions hydrogen bond |
| url | https://journals.iucr.org/paper?S205698902500012X |
| work_keys_str_mv | AT atashvgurbanov synthesescrystalstructureshirshfeldsurfaceanalysesandcrystalvoidsof14bromophenyl22dichloroethan1oneand22dibromo1ptolylethan1one AT firudiniguseinov synthesescrystalstructureshirshfeldsurfaceanalysesandcrystalvoidsof14bromophenyl22dichloroethan1oneand22dibromo1ptolylethan1one AT aidaisamigullina synthesescrystalstructureshirshfeldsurfaceanalysesandcrystalvoidsof14bromophenyl22dichloroethan1oneand22dibromo1ptolylethan1one AT tuncerhokelek synthesescrystalstructureshirshfeldsurfaceanalysesandcrystalvoidsof14bromophenyl22dichloroethan1oneand22dibromo1ptolylethan1one AT khudayarihasanov synthesescrystalstructureshirshfeldsurfaceanalysesandcrystalvoidsof14bromophenyl22dichloroethan1oneand22dibromo1ptolylethan1one AT tahirajavadzade synthesescrystalstructureshirshfeldsurfaceanalysesandcrystalvoidsof14bromophenyl22dichloroethan1oneand22dibromo1ptolylethan1one AT alebelnbelay synthesescrystalstructureshirshfeldsurfaceanalysesandcrystalvoidsof14bromophenyl22dichloroethan1oneand22dibromo1ptolylethan1one |