Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one
The title compound, C15H15NO2, is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intramolecular N—H...O hydrogen bond present forming an S(6...
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International Union of Crystallography
2019-06-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019006583 |
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doaj-8067700ecccc48b0b29fea5993b5ff9f2020-11-24T21:40:22ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-06-0175678578810.1107/S2056989019006583wm5504Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-oneSevgi Kansiz0Alev Sema Aydin1Necmi Dege2Erbil Agar3Igor O. Fritsky4Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Kurupelit, Samsun, TurkeyOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, TurkeyOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, TurkeyOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, TurkeyTaras Shevchenko National University of Kyiv, Department of Chemistry, 64, Vladimirska Str., Kiev 01601, UkraineThe title compound, C15H15NO2, is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intramolecular N—H...O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O—H...O hydrogen bonds link adjacent molecules into inversion dimers with an R22(18) ring motif. The dimers are linked by very weak π–π interactions, forming layers parallel to (\overline{2}01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surfaces were used to analyse the intermolecular interactions, indicating that the most important contributions for the crystal packing are from H...H (55.2%), C...H/H...C (22.3%) and O...H/H...O (13.6%) interactions.http://scripts.iucr.org/cgi-bin/paper?S2056989019006583crystal structureSchiff basehydrogen bondingHirshfeld surface analysis |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Sevgi Kansiz Alev Sema Aydin Necmi Dege Erbil Agar Igor O. Fritsky |
| spellingShingle |
Sevgi Kansiz Alev Sema Aydin Necmi Dege Erbil Agar Igor O. Fritsky Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one Acta Crystallographica Section E: Crystallographic Communications crystal structure Schiff base hydrogen bonding Hirshfeld surface analysis |
| author_facet |
Sevgi Kansiz Alev Sema Aydin Necmi Dege Erbil Agar Igor O. Fritsky |
| author_sort |
Sevgi Kansiz |
| title |
Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
| title_short |
Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
| title_full |
Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
| title_fullStr |
Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
| title_full_unstemmed |
Crystal structure and Hirshfeld surface analysis of (Z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
| title_sort |
crystal structure and hirshfeld surface analysis of (z)-6-[(2-hydroxy-4-methylanilino)methylidene]-4-methylcyclohexa-2,4-dien-1-one |
| publisher |
International Union of Crystallography |
| series |
Acta Crystallographica Section E: Crystallographic Communications |
| issn |
2056-9890 |
| publishDate |
2019-06-01 |
| description |
The title compound, C15H15NO2, is a Schiff base that exists in the keto–enamine tautomeric form and adopts a Z configuration. The molecule is almost planar, with the two phenyl rings twisted relative to each other by 9.60 (18)°. There is an intramolecular N—H...O hydrogen bond present forming an S(6) ring motif. In the crystal, pairs of O—H...O hydrogen bonds link adjacent molecules into inversion dimers with an R22(18) ring motif. The dimers are linked by very weak π–π interactions, forming layers parallel to (\overline{2}01). Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surfaces were used to analyse the intermolecular interactions, indicating that the most important contributions for the crystal packing are from H...H (55.2%), C...H/H...C (22.3%) and O...H/H...O (13.6%) interactions. |
| topic |
crystal structure Schiff base hydrogen bonding Hirshfeld surface analysis |
| url |
http://scripts.iucr.org/cgi-bin/paper?S2056989019006583 |
| work_keys_str_mv |
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