2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry
The title compound, C15H13BrO2S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromophenyl)sulfanyl, benzaldehyde and methoxy residues: crystal symmetry generates a racemic mixture. A twist in the molecule is evident about the methine-C—C(carbonyl) bo...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2019
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| Online Access: | http://eprints.sunway.edu.my/1043/ http://eprints.sunway.edu.my/1043/1/Tiekink%202-4%20Bromophenyl%20ActaCryst%202019%20E75%20816.pdf |
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| author | Caracelli, Ignez Zukerman-Schpector, Julio Traesel, Henrique J. Olivato, Paulo R. Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_facet | Caracelli, Ignez Zukerman-Schpector, Julio Traesel, Henrique J. Olivato, Paulo R. Jotani, Mukesh M. Tiekink, Edward R. T. * |
| author_sort | Caracelli, Ignez |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The title compound, C15H13BrO2S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromophenyl)sulfanyl, benzaldehyde and methoxy residues: crystal symmetry generates a racemic mixture. A twist in the molecule is evident about the methine-C—C(carbonyl) bond as evidenced by the O—C—C—O torsion angle of -20.8 (7)⁰. The dihedral angle between the bromobenzene and phenyl rings is 43.2 (2)⁰, with the former disposed to lie over the oxygen atoms. The most prominent feature of the packing is the formation of helical supramolecular chains as a result of methyland methine-C—H...O(carbonyl) interactions. The chains assemble into a three-dimensional architecture without directional interactions between them. The nature of the weak points of contacts has been probed by a combination of Hirshfeld surface analysis, non-covalent interaction plots and interaction energy calculations. These point to the importance of weaker H...H and C—H...C interactions in the consolidation of the structure. |
| first_indexed | 2025-11-14T21:15:34Z |
| format | Article |
| id | sunway-1043 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:15:34Z |
| publishDate | 2019 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-10432020-10-07T08:38:35Z http://eprints.sunway.edu.my/1043/ 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry Caracelli, Ignez Zukerman-Schpector, Julio Traesel, Henrique J. Olivato, Paulo R. Jotani, Mukesh M. Tiekink, Edward R. T. * QD Chemistry The title compound, C15H13BrO2S, comprises three different substituents bound to a central (and chiral) methine-C atom, i.e. (4-bromophenyl)sulfanyl, benzaldehyde and methoxy residues: crystal symmetry generates a racemic mixture. A twist in the molecule is evident about the methine-C—C(carbonyl) bond as evidenced by the O—C—C—O torsion angle of -20.8 (7)⁰. The dihedral angle between the bromobenzene and phenyl rings is 43.2 (2)⁰, with the former disposed to lie over the oxygen atoms. The most prominent feature of the packing is the formation of helical supramolecular chains as a result of methyland methine-C—H...O(carbonyl) interactions. The chains assemble into a three-dimensional architecture without directional interactions between them. The nature of the weak points of contacts has been probed by a combination of Hirshfeld surface analysis, non-covalent interaction plots and interaction energy calculations. These point to the importance of weaker H...H and C—H...C interactions in the consolidation of the structure. International Union of Crystallography 2019-05-11 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1043/1/Tiekink%202-4%20Bromophenyl%20ActaCryst%202019%20E75%20816.pdf Caracelli, Ignez and Zukerman-Schpector, Julio and Traesel, Henrique J. and Olivato, Paulo R. and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2019) 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry. Acta Crystallographica Section E Crystallographic Communications, 75 (6). pp. 816-822. ISSN 2056-9890 (In Press) http://doi.org/10.1107/S2056989019006765 doi:10.1107/S2056989019006765 |
| spellingShingle | QD Chemistry Caracelli, Ignez Zukerman-Schpector, Julio Traesel, Henrique J. Olivato, Paulo R. Jotani, Mukesh M. Tiekink, Edward R. T. * 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title | 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_full | 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_fullStr | 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_full_unstemmed | 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_short | 2-[(4-Bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_sort | 2-[(4-bromophenyl)sulfanyl]-2-methoxy-1-phenylethan-1-one: crystal structure, hirshfeld surface analysis and computational chemistry |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1043/ http://eprints.sunway.edu.my/1043/ http://eprints.sunway.edu.my/1043/ http://eprints.sunway.edu.my/1043/1/Tiekink%202-4%20Bromophenyl%20ActaCryst%202019%20E75%20816.pdf |