Crystal structure of benzyl 3-(3-methyl-phenyl) dithiocarbazate

NurFadhilah Abdul Aziz; Enis Nadia Md Yusof; Thahira Begum S A Ravoof; Edward R T Tiekink; W.T.A. Harrison

doi:10.1107/S2056989015004764

Crystal structure of benzyl 3-(3-methyl-phenyl) dithiocarbazate

NurFadhilah Abdul Aziz, Enis Nadia Md Yusof, Thahira Begum S A Ravoof^*, Edward R T Tiekink, W.T.A. Harrison (Editor)

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article

Abstract

In the title compound, C₁₅H₁₆N₂S₂, the central CN₂S₂ residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N - N bond is gauche [C - N - N - C = - 117.48 (15)°]. Overall, the molecule has the shape of the letter L. In the crystal packing, supramolecular chains along the a axis are formed by N - H⋯S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {⋯HNCS}₂ and 10-membered {⋯HNNH⋯S}₂ synthons. The chains are connected into layers by phenyl-tolyl C - H⋯π interactions; the layers stack along the c axis with no specific interactions between them.

Original language	English
Pages (from-to)	o233-o234
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	4
Early online date	14 Mar 2015
DOIs	https://doi.org/10.1107/S2056989015004764
Publication status	Published - 1 Apr 2015

Keywords

C - H⋯πinteractions
Crystal structure
Hydrogen bonding
S-substituted dithiocarbazate

ASJC Scopus subject areas

Condensed Matter Physics
Materials Science(all)
Chemistry(all)

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Aziz, N. A., Yusof, E. N. M., Ravoof, T. B. S. A., Tiekink, E. R. T., & Harrison, W. T. A. (Ed.) (2015). Crystal structure of benzyl 3-(3-methyl-phenyl) dithiocarbazate. Acta Crystallographica Section E: Structure Reports Online, 71(4), o233-o234. https://doi.org/10.1107/S2056989015004764

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title = "Crystal structure of benzyl 3-(3-methyl-phenyl) dithiocarbazate",

abstract = "In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 {\AA}) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N - N bond is gauche [C - N - N - C = - 117.48 (15)°]. Overall, the molecule has the shape of the letter L. In the crystal packing, supramolecular chains along the a axis are formed by N - H⋯S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {⋯HNCS}2 and 10-membered {⋯HNNH⋯S}2 synthons. The chains are connected into layers by phenyl-tolyl C - H⋯π interactions; the layers stack along the c axis with no specific interactions between them.",

keywords = "C - H⋯πinteractions, Crystal structure, Hydrogen bonding, S-substituted dithiocarbazate",

author = "Aziz, {NurFadhilah Abdul} and Yusof, {Enis Nadia Md} and Ravoof, {Thahira Begum S A} and Tiekink, {Edward R T} and W.T.A. Harrison",

note = "Support for the project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS No. 9419400) and the Science Fund under the Ministry of Science, Technology and Innovation (MOSTI) (06-01-04-SF1810). We also wish to thank Ms Khadijah Densabali for collecting the intensity data. NFAA wishes to thank UPM for the Graduate Research Fellowship award.",

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T1 - Crystal structure of benzyl 3-(3-methyl-phenyl) dithiocarbazate

AU - Aziz, NurFadhilah Abdul

AU - Yusof, Enis Nadia Md

AU - Ravoof, Thahira Begum S A

AU - Tiekink, Edward R T

A2 - Harrison, W.T.A.

N1 - Support for the project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS No. 9419400) and the Science Fund under the Ministry of Science, Technology and Innovation (MOSTI) (06-01-04-SF1810). We also wish to thank Ms Khadijah Densabali for collecting the intensity data. NFAA wishes to thank UPM for the Graduate Research Fellowship award.

PY - 2015/4/1

Y1 - 2015/4/1

N2 - In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N - N bond is gauche [C - N - N - C = - 117.48 (15)°]. Overall, the molecule has the shape of the letter L. In the crystal packing, supramolecular chains along the a axis are formed by N - H⋯S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {⋯HNCS}2 and 10-membered {⋯HNNH⋯S}2 synthons. The chains are connected into layers by phenyl-tolyl C - H⋯π interactions; the layers stack along the c axis with no specific interactions between them.

AB - In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N - N bond is gauche [C - N - N - C = - 117.48 (15)°]. Overall, the molecule has the shape of the letter L. In the crystal packing, supramolecular chains along the a axis are formed by N - H⋯S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {⋯HNCS}2 and 10-membered {⋯HNNH⋯S}2 synthons. The chains are connected into layers by phenyl-tolyl C - H⋯π interactions; the layers stack along the c axis with no specific interactions between them.

KW - C - H⋯πinteractions

KW - Crystal structure

KW - Hydrogen bonding

KW - S-substituted dithiocarbazate

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