S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis

In the title dithiocarbazate ester, C 16 H 17 N 3 S 2 (systematic name: ( Z )-{[(benzylsulfanyl)methanethioyl]amino}[1-(6-methylpyridin-2-yl)ethylidene]amine), the central methylidenehydrazinecarbodithioate (C 2 N 2 S 2 ) core is almost planar (r.m.s. deviation = 0.0111 Å) and forms dihedral angles...

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Main Authors: Omar, Siti Aminah, Chah, Chee Keong, Ravoof, Thahira Begum S. A., Jonita, Mukesh M., Tiekink, Edward R. T.
Format: Article
Language:English
Published: International Union of Crystallography 2018
Online Access:http://psasir.upm.edu.my/id/eprint/73830/1/S%20Benzy%203%20%5B1%20%286methylpyridin%202%20yl%29ethylidene%5D%20dithiocarbazate%20crystal%20structure%20and%20Hirshfeld%20surface%20analysis.pdf
http://psasir.upm.edu.my/id/eprint/73830/
https://journals.iucr.org/e/issues/2018/02/00/hb7730/
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spelling my.upm.eprints.738302021-12-02T07:12:08Z http://psasir.upm.edu.my/id/eprint/73830/ S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis Omar, Siti Aminah Chah, Chee Keong Ravoof, Thahira Begum S. A. Jonita, Mukesh M. Tiekink, Edward R. T. In the title dithiocarbazate ester, C 16 H 17 N 3 S 2 (systematic name: ( Z )-{[(benzylsulfanyl)methanethioyl]amino}[1-(6-methylpyridin-2-yl)ethylidene]amine), the central methylidenehydrazinecarbodithioate (C 2 N 2 S 2 ) core is almost planar (r.m.s. deviation = 0.0111 Å) and forms dihedral angles of 71.67 (3)° with the approximately orthogonally inclined thioester phenyl ring, and 7.16 (7)° with the approximately coplanar substituted pyridyl ring. The latter arrangement and the Z configuration about the imine-C=N bond allows for the formation of an intramolecular hydrazine-N—H...N(pyridyl) hydrogen bond that closes an S (6) loop. In the crystal, phenyl-C—H...S(thione), methylene-C—H...π(pyridyl), methylene- and phenyl-C—H...π(phenyl) contacts connect molecules into supramolecular layers propagating in the bc plane; the layers stack along the a axis with no directional interactions between them. The analysis of the Hirshfeld surface indicates the relative importance of an intralayer phenyl-H...H(pyridyl) contact upon the molecular packing. International Union of Crystallography 2018 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/73830/1/S%20Benzy%203%20%5B1%20%286methylpyridin%202%20yl%29ethylidene%5D%20dithiocarbazate%20crystal%20structure%20and%20Hirshfeld%20surface%20analysis.pdf Omar, Siti Aminah and Chah, Chee Keong and Ravoof, Thahira Begum S. A. and Jonita, Mukesh M. and Tiekink, Edward R. T. (2018) S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis. Acta Crystallographica Section E: Crystallographic Communications, 74. art. no. pt. 2. 261 - 266. ISSN 2056-9890 https://journals.iucr.org/e/issues/2018/02/00/hb7730/ 10.1107/S2056989018001330
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description In the title dithiocarbazate ester, C 16 H 17 N 3 S 2 (systematic name: ( Z )-{[(benzylsulfanyl)methanethioyl]amino}[1-(6-methylpyridin-2-yl)ethylidene]amine), the central methylidenehydrazinecarbodithioate (C 2 N 2 S 2 ) core is almost planar (r.m.s. deviation = 0.0111 Å) and forms dihedral angles of 71.67 (3)° with the approximately orthogonally inclined thioester phenyl ring, and 7.16 (7)° with the approximately coplanar substituted pyridyl ring. The latter arrangement and the Z configuration about the imine-C=N bond allows for the formation of an intramolecular hydrazine-N—H...N(pyridyl) hydrogen bond that closes an S (6) loop. In the crystal, phenyl-C—H...S(thione), methylene-C—H...π(pyridyl), methylene- and phenyl-C—H...π(phenyl) contacts connect molecules into supramolecular layers propagating in the bc plane; the layers stack along the a axis with no directional interactions between them. The analysis of the Hirshfeld surface indicates the relative importance of an intralayer phenyl-H...H(pyridyl) contact upon the molecular packing.
format Article
author Omar, Siti Aminah
Chah, Chee Keong
Ravoof, Thahira Begum S. A.
Jonita, Mukesh M.
Tiekink, Edward R. T.
spellingShingle Omar, Siti Aminah
Chah, Chee Keong
Ravoof, Thahira Begum S. A.
Jonita, Mukesh M.
Tiekink, Edward R. T.
S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis
author_facet Omar, Siti Aminah
Chah, Chee Keong
Ravoof, Thahira Begum S. A.
Jonita, Mukesh M.
Tiekink, Edward R. T.
author_sort Omar, Siti Aminah
title S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis
title_short S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis
title_full S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis
title_fullStr S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis
title_full_unstemmed S-Benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and Hirshfeld surface analysis
title_sort s-benzyl 3-[1-(6-methylpyridin-2-yl)ethylidene]- dithiocarbazate: crystal structure and hirshfeld surface analysis
publisher International Union of Crystallography
publishDate 2018
url http://psasir.upm.edu.my/id/eprint/73830/1/S%20Benzy%203%20%5B1%20%286methylpyridin%202%20yl%29ethylidene%5D%20dithiocarbazate%20crystal%20structure%20and%20Hirshfeld%20surface%20analysis.pdf
http://psasir.upm.edu.my/id/eprint/73830/
https://journals.iucr.org/e/issues/2018/02/00/hb7730/
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