2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis
The title dithiocarbazate ester, C16H16N2O2S2, comprises two almost planar residues, i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intramolecular hydroxy-O—H⋯N(imine) hydrogen...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2016
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| Online Access: | http://psasir.upm.edu.my/id/eprint/54801/ http://psasir.upm.edu.my/id/eprint/54801/1/2-%5B%281E%29-%28%7B%5B%28Benzylsulfanyl%29methanethioyl%5Damino%7D-.pdf |
| _version_ | 1848852632994578432 |
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| author | Md Yusof, Enis Nadia Jotani, Mukesh M. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. |
| author_facet | Md Yusof, Enis Nadia Jotani, Mukesh M. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. |
| author_sort | Md Yusof, Enis Nadia |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | The title dithiocarbazate ester, C16H16N2O2S2, comprises two almost planar residues, i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intramolecular hydroxy-O—H⋯N(imine) hydrogen bond, leading to an S(6) loop, is noted. An analysis of the geometric parameters is consistent with the molecule existing as the thione tautomer, and the conformation about the C=N bond is E. The thione S and imine H atoms lie to the same side of the molecule, facilitating the formation of intermolecular N—H⋯S hydrogen bonds leading to eight-membered {⋯HNCS}2 synthons in the crystal. These aggregates are connected by phenyl-C—H⋯O(hydroxy) interactions into a supramolecular layer in the bc plane; these stack with no directional interactions between them. An analysis of the Hirshfeld surface confirms the nature of the intermolecular interactions. |
| first_indexed | 2025-11-15T10:41:10Z |
| format | Article |
| id | upm-54801 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T10:41:10Z |
| publishDate | 2016 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-548012017-07-06T05:40:30Z http://psasir.upm.edu.my/id/eprint/54801/ 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis Md Yusof, Enis Nadia Jotani, Mukesh M. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. The title dithiocarbazate ester, C16H16N2O2S2, comprises two almost planar residues, i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intramolecular hydroxy-O—H⋯N(imine) hydrogen bond, leading to an S(6) loop, is noted. An analysis of the geometric parameters is consistent with the molecule existing as the thione tautomer, and the conformation about the C=N bond is E. The thione S and imine H atoms lie to the same side of the molecule, facilitating the formation of intermolecular N—H⋯S hydrogen bonds leading to eight-membered {⋯HNCS}2 synthons in the crystal. These aggregates are connected by phenyl-C—H⋯O(hydroxy) interactions into a supramolecular layer in the bc plane; these stack with no directional interactions between them. An analysis of the Hirshfeld surface confirms the nature of the intermolecular interactions. International Union of Crystallography 2016-04-01 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/54801/1/2-%5B%281E%29-%28%7B%5B%28Benzylsulfanyl%29methanethioyl%5Damino%7D-.pdf Md Yusof, Enis Nadia and Jotani, Mukesh M. and Tiekink, Edward R. T. and Ravoof, Thahira B. S. A. (2016) 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E: Crystallographic Communications, E72 (1). pp. 516-521. ISSN 2056-9890 https://journals.iucr.org/e/issues/2016/04/00/hb7572/hb7572.pdf 10.1107/S2056989016004291 |
| spellingShingle | Md Yusof, Enis Nadia Jotani, Mukesh M. Tiekink, Edward R. T. Ravoof, Thahira B. S. A. 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
| title | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
| title_full | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
| title_fullStr | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
| title_full_unstemmed | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
| title_short | 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis |
| title_sort | 2-[(1e)-({[(benzylsulfanyl)methanethioyl]amino}- imino)methyl]-6-methoxyphenol: crystal structure and hirshfeld surface analysis |
| url | http://psasir.upm.edu.my/id/eprint/54801/ http://psasir.upm.edu.my/id/eprint/54801/ http://psasir.upm.edu.my/id/eprint/54801/ http://psasir.upm.edu.my/id/eprint/54801/1/2-%5B%281E%29-%28%7B%5B%28Benzylsulfanyl%29methanethioyl%5Damino%7D-.pdf |