2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study
The complete molecule of the title hydrazine carbodithioate derivative, C32H30N4O2S4, is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule is twisted about this bond with the C—S—S—C torsion angle of 90.70 (8)⁰ indicating an orthogonal relationship between the...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2020
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| Online Access: | http://eprints.sunway.edu.my/1328/ http://eprints.sunway.edu.my/1328/1/Tiekink%20Acta%20Cryst%202020%20E76%201245.pdf |
| _version_ | 1848802029927923712 |
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| author | Paulus, G. Kwong, Huey Chong * Crouse, Karen A. Tiekink, Edward R. T. * |
| author_facet | Paulus, G. Kwong, Huey Chong * Crouse, Karen A. Tiekink, Edward R. T. * |
| author_sort | Paulus, G. |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The complete molecule of the title hydrazine carbodithioate derivative, C32H30N4O2S4, is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule is twisted about this bond with the C—S—S—C torsion angle of 90.70 (8)⁰ indicating an orthogonal relationship between the symmetry-related halves of the molecule. The conformation about the imine bond [1.282 (2) A ˚ ] isE and there is limited delocalization of π-electron density over the CN2C residue as there is a twist about the N—N bond [C—N—N—C torsion angle = -166.57 (15)⁰]. An intramolecular hydroxyl-O—H...N(imine) hydrogen bond closes an S(6) loop. In the crystal, methylene-C—H...π(tolyl) contacts assemble molecules into a supramolecular layer propagating in the ab plane: the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of H...H contacts, which contribute 46.7% of all contacts followed by H...C/C...H contacts [25.5%] reflecting, in part, the C—H...π(tolyl) contacts. The calculation of the interaction energies confirm the importance of the dispersion term and the influence of the stabilizing H...H contacts in the inter-layer region. |
| first_indexed | 2025-11-14T21:16:52Z |
| format | Article |
| id | sunway-1328 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:16:52Z |
| publishDate | 2020 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-13282020-10-07T07:00:09Z http://eprints.sunway.edu.my/1328/ 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study Paulus, G. Kwong, Huey Chong * Crouse, Karen A. Tiekink, Edward R. T. * QD Chemistry The complete molecule of the title hydrazine carbodithioate derivative, C32H30N4O2S4, is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule is twisted about this bond with the C—S—S—C torsion angle of 90.70 (8)⁰ indicating an orthogonal relationship between the symmetry-related halves of the molecule. The conformation about the imine bond [1.282 (2) A ˚ ] isE and there is limited delocalization of π-electron density over the CN2C residue as there is a twist about the N—N bond [C—N—N—C torsion angle = -166.57 (15)⁰]. An intramolecular hydroxyl-O—H...N(imine) hydrogen bond closes an S(6) loop. In the crystal, methylene-C—H...π(tolyl) contacts assemble molecules into a supramolecular layer propagating in the ab plane: the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of H...H contacts, which contribute 46.7% of all contacts followed by H...C/C...H contacts [25.5%] reflecting, in part, the C—H...π(tolyl) contacts. The calculation of the interaction energies confirm the importance of the dispersion term and the influence of the stabilizing H...H contacts in the inter-layer region. International Union of Crystallography 2020-06-30 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1328/1/Tiekink%20Acta%20Cryst%202020%20E76%201245.pdf Paulus, G. and Kwong, Huey Chong * and Crouse, Karen A. and Tiekink, Edward R. T. * (2020) 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study. Acta Crystallographica Section E Crystallographic Communications, 76 (8). pp. 1245-1250. ISSN 2056-9890 (In Press) http://doi.org/10.1107/S2056989020008762 doi:10.1107/S2056989020008762 |
| spellingShingle | QD Chemistry Paulus, G. Kwong, Huey Chong * Crouse, Karen A. Tiekink, Edward R. T. * 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_full | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_fullStr | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_full_unstemmed | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_short | 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study |
| title_sort | 2-[(1e)-[(z)-2-({[(1z)-[(e)-2-[(2-hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, hirshfeld surface analysis and computational study |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1328/ http://eprints.sunway.edu.my/1328/ http://eprints.sunway.edu.my/1328/ http://eprints.sunway.edu.my/1328/1/Tiekink%20Acta%20Cryst%202020%20E76%201245.pdf |