1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry
The crystal and molecular structures of C14H12Cl2, (I), and C14H12Br2, (II), are described. The asymmetric unit of (I) comprises two independent molecules, A and B, each disposed about a centre of inversion. Each molecule approximates mirror symmetry [the Cb—Cb—Ce—Ce torsion angles = 83.46 (19) and...
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International Union of Crystallographic
2019
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| Online Access: | http://eprints.sunway.edu.my/1028/ http://eprints.sunway.edu.my/1028/1/Tiekink%201%20Chloro%204%202%204%20chlorophenyl%20Acta%20Cryst%20%282019%29%20E75%20624.pdf |
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| author | Jotani, Mukesh M. Lee, See Mun * Lo, Kong Mun * Tiekink, Edward R. T. * |
| author_facet | Jotani, Mukesh M. Lee, See Mun * Lo, Kong Mun * Tiekink, Edward R. T. * |
| author_sort | Jotani, Mukesh M. |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The crystal and molecular structures of C14H12Cl2, (I), and C14H12Br2, (II), are described. The asymmetric unit of (I) comprises two independent molecules, A and B, each disposed about a centre of inversion. Each molecule approximates mirror symmetry [the Cb—Cb—Ce—Ce torsion angles = 83.46 (19) and 95.17 (17) for A, and 83.7 (2) and 94.75 (19) for B; b = benzene and e = ethylene]. By contrast, the molecule in (II) is twisted, as seen in the dihedral angle of 59.29 (11) between the benzene rings cf. 0 in (I). The molecular packing of (I) features benzene-C—H...π(benzene) and Cl...Cl contacts that lead to an open three-dimensional (3D) architecture that enables twofold 3D–3D interpenetration. The presence of benzene-C—H...π(benzene) and Br...Br contacts in the crystal of (II) consolidate the 3D architecture. The analysis of the
calculated Hirshfeld surfaces confirm the influence of the benzene-C—H...π(benzene) and X...X contacts on the molecular packing and show that, to a first approximation, H...H, C...H/H...C and C...X/X...C contacts dominate the packing, each contributing about 30% to the overall surface in each of (I) and (II). The analysis also clearly differentiates between the A and B molecules of (I). |
| first_indexed | 2025-11-14T21:15:30Z |
| format | Article |
| id | sunway-1028 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:15:30Z |
| publishDate | 2019 |
| publisher | International Union of Crystallographic |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-10282020-10-07T08:42:54Z http://eprints.sunway.edu.my/1028/ 1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry Jotani, Mukesh M. Lee, See Mun * Lo, Kong Mun * Tiekink, Edward R. T. * QD Chemistry The crystal and molecular structures of C14H12Cl2, (I), and C14H12Br2, (II), are described. The asymmetric unit of (I) comprises two independent molecules, A and B, each disposed about a centre of inversion. Each molecule approximates mirror symmetry [the Cb—Cb—Ce—Ce torsion angles = 83.46 (19) and 95.17 (17) for A, and 83.7 (2) and 94.75 (19) for B; b = benzene and e = ethylene]. By contrast, the molecule in (II) is twisted, as seen in the dihedral angle of 59.29 (11) between the benzene rings cf. 0 in (I). The molecular packing of (I) features benzene-C—H...π(benzene) and Cl...Cl contacts that lead to an open three-dimensional (3D) architecture that enables twofold 3D–3D interpenetration. The presence of benzene-C—H...π(benzene) and Br...Br contacts in the crystal of (II) consolidate the 3D architecture. The analysis of the calculated Hirshfeld surfaces confirm the influence of the benzene-C—H...π(benzene) and X...X contacts on the molecular packing and show that, to a first approximation, H...H, C...H/H...C and C...X/X...C contacts dominate the packing, each contributing about 30% to the overall surface in each of (I) and (II). The analysis also clearly differentiates between the A and B molecules of (I). International Union of Crystallographic 2019-04-08 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1028/1/Tiekink%201%20Chloro%204%202%204%20chlorophenyl%20Acta%20Cryst%20%282019%29%20E75%20624.pdf Jotani, Mukesh M. and Lee, See Mun * and Lo, Kong Mun * and Tiekink, Edward R. T. * (2019) 1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry. Acta Crystallographica Section E Crystallographic Communications, 75 (5). pp. 624-631. ISSN 2056-9890 (In Press) http://doi.org/10.1107/S2056989019004742 doi:10.1107/S2056989019004742 |
| spellingShingle | QD Chemistry Jotani, Mukesh M. Lee, See Mun * Lo, Kong Mun * Tiekink, Edward R. T. * 1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title | 1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_full | 1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_fullStr | 1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_full_unstemmed | 1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_short | 1-Chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, Hirshfeld surface analysis and computational chemistry |
| title_sort | 1-chloro-4-[2-(4-chlorophenyl)ethyl]benzene and its bromo analogue: crystal structure, hirshfeld surface analysis and computational chemistry |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1028/ http://eprints.sunway.edu.my/1028/ http://eprints.sunway.edu.my/1028/ http://eprints.sunway.edu.my/1028/1/Tiekink%201%20Chloro%204%202%204%20chlorophenyl%20Acta%20Cryst%20%282019%29%20E75%20624.pdf |