Crystal structure of (Z)-4-methylbenzyl 3-[1-(5-methylpyridin-2-yl)ethylidene]dithiocarbazate

Abstract

In the title di­thio­carbazate compound, C17H19N3S2, the central CN2S2 residue is essentially planar (r.m.s. deviation = 0.0288 Å) and forms dihedral angles of 9.77 (8) and 77.47 (7)° with the substituted-pyridyl and p-tolyl rings, respectively, indicating a highly twisted mol­ecule; the dihedral angle between the rings is 85.56 (8)°. The configuration about the C=N bond is Z, which allows for the formation of an intra­molecular N—H⋯N(pyrid­yl) hydrogen bond. The packing features tolyl-methyl-C—H⋯N(imine), pyridyl-C—H⋯π(tol­yl) and π–π inter­actions [between pyridyl rings with a distance = 3.7946 (13) Å], which generates jagged supra­molecular layers that stack along the b axis with no directional inter­actions between them.

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

“…As mentioned in the Chemical context, there is sustained interest in this class of compound and this is reflected by the observation there are four closely related structures available for comparison, varying in the S-bound group and substitution in the 2-pyridyl ring. In common with (I), the derivative with the 4-methylbenzyl ester and with a methyl group in the 5-position of the pyridyl ring, a Z-configuration is noted about the imine bond allowing for the formation of an intramolecular hydrazine-N-HÁ Á ÁN(pyridyl) hydrogen bond (Ravoof et al, 2015). By contrast, the three remaining analogues, i.e.…”

Crystal structure of benzyl N′-[(1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-ylidene]hydrazine-1-carbodithioate

“…In contrast to most of the structures, torsion angle 11 = 17.1 for WADGAK indicates a syn-periplanar conformation. (Manan et al, 2011) 5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidenyl À178.5 À9.1 176.9 À108.0 À84.1 ABOSAN (Manan et al, 2011) 5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidenyl À178.8 À7.7 177.5 À110.4 À81.8 BAHWIT (Md Yusof et al, 2015) 2-methoxybenzylidenyl À179.1 2.6 À178.0 À177.7 À85.7 BAHWOZ (Md Yusof et al, 2015) 3-methoxybenzylidenyl À178.0 À1.2 À178.1 173.8 À80.1 CEFBIB (Islam et al, 2016a) 2,4,5-trimethoxybenzylidenyl 179.6 À5.2 À177.9 173.4 À79.7 COBQUH (Mirza et al, 2014) pyridin-2-ylmethylenyl À177.2 À5.3 À177.2 À176.0 À68.7 DATFEK (Khoo et al, 2005) furan-2-yl)ethylidenyl 178.6 1.7 180.0 180.0 À72.5 EDETUD (How et al, 2007) 1-(3-pyridyl)ethylidenyl À179.2 4.9 À179.8 À165.8 À87.5 EHIXUQ (Yusof et al, 2016) 2-hydroxy-3-methoxybenzylidenyl 177.4 1.8 179.9 À173.3 À101.2 EMEBAA (Ravoof et al, 2011) bis ( (Omar et al, 2018) 1-(6-methylpyridin-2-yl)ethylidenyl À177.7 À1.6 À176.0 171.6 À108.0 IFUTUZ (Khaledi et al, 2008a) 1 H-indol-3-ylmethylidenyl À172.7 2.6 179.0 103.7 À68.2 JAMMOA (Ali et al, 2004) quinolinyl-2-methylenyl 177.9 0.8 177.5 À171.0 101.8 KAGZOK (Ravoof et al, 2015) 1-(5-methylpyridin-2-yl)ethylidenyl À176.9 À5.6 À173.2 164.7 À77.8 KUCRAC (Hamid et al, 2009) 1-(pyrazin-2-yl)ethylidenyl 178.4 0.6 178.8 174.7 À70.0 KUCZUD (Xu et al, 1991) pyridine-N-oxide-2-yl)methylidenyl À171.4 À2.0 176.5 À161.7 À92.2 LOBSEB (Shan et al, 2008b) furan-2-ylmethylenyl 173.8 À0.5 179.7 177.1 À93.0 LOBVOO (Tarafder et al, 2008) ( Ali et al, 2011) bis(pyridin-2-yl)methylenyl 165.1 1.9 À177.2 À180.0 À83.8 PEWLEL (Li et al, 2012) phenyl(pyridin-2-yl)methylenyl À177.0 4.6 À173.1 87.6 À119.2 QORJAK (Tan et al, 2015) 3 (Li et al, 2009) 3-nitrobenzylidenyl 178.3 À2.9 À177.5 173.1 À85.5 SALSEE (Zhang et al, 2004) 4-((2-hydroxyethyl)methylamino)benzylidenyl À166.4 0.9 À176.8 170.4 À88.4 SIMMUX (Qiu & Luo, 2007) 2 (Islam et al, 2016b) 3,4,5-trimethoxybenzylidenyl À179.4 À5.1 À177.1 174.9 À73.3 TIFSEH (Roy et al, 2007) 2-methylthio-6-methyl-4-pyrimidyl)methylenyl …”