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A cinnamaldehyde Schiff base of S -(4-methyl ­ benz ­ yl) di ­ thio ­ carbazate: crystal structure, Hirshfeld surface analysis and computational study

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ABSTRACT

The title di­thio­carbazate ester (I), C18H18N2S2 [systematic name: (E)-4-methyl­benzyl 2-[(E)-3-phenyl­allyl­idene]hydrazinecarbodi­thio­ate, comprises an almost planar central CN2S2 residue [r.m.s. deviation = 0.0131 Å]. The methyl­ene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the mol­ecule approximates mirror symmetry with the 4-tolyl group bis­ected by the plane. The configuration about both double bonds in the N—N=C—C=C chain is E; the chain has an all trans conformation. In the crystal, eight-membered centrosymmetric thio­amide synthons, {⋯HNCS}2, are formed via N—H⋯S(thione) hydrogen bonds. Connections between the dimers via C—H⋯π inter­actions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an inter­action profile similar to that of a closely related analogue with an S-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connected via N—H⋯S hydrogen bonds is about 0.94 kcal mol−1 more stable than that in (I).

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Mol­ecular packing in (I): (a) a view of the supra­molecular dimer sustained by N—H⋯S(thione) hydrogen bonds and (b) a view of the unit-cell contents shown in projection down the a axis. The N—H⋯S and C—H⋯π inter­actions are shown as orange and purple dashed lines, respectively.
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fig2: Mol­ecular packing in (I): (a) a view of the supra­molecular dimer sustained by N—H⋯S(thione) hydrogen bonds and (b) a view of the unit-cell contents shown in projection down the a axis. The N—H⋯S and C—H⋯π inter­actions are shown as orange and purple dashed lines, respectively.

Mentions: The most prominent feature of the mol­ecular packing is the formation of an eight-membered, centrosymmetric thio­amide synthon, {⋯HNCS}2 mediated by N—H⋯S(thione) hydrogen bonds, Fig. 2 ▸a and Table 1 ▸. The dimeric aggregates thus formed are connected into a three-dimensional architecture, Fig. 2 ▸b, via methyl­ene-C—H⋯π(tol­yl), tolyl-C—H⋯π(phen­yl) and phenyl-C—H⋯π(tol­yl) inter­actions, Table 1 ▸, indicating the tolyl ring accepts two such contacts. In essence, the C—H⋯π inter­actions connect mol­ecules into layers in the bc plane and these are linked by the N—H⋯S hydrogen bonds.


A cinnamaldehyde Schiff base of S -(4-methyl ­ benz ­ yl) di ­ thio ­ carbazate: crystal structure, Hirshfeld surface analysis and computational study
Mol­ecular packing in (I): (a) a view of the supra­molecular dimer sustained by N—H⋯S(thione) hydrogen bonds and (b) a view of the unit-cell contents shown in projection down the a axis. The N—H⋯S and C—H⋯π inter­actions are shown as orange and purple dashed lines, respectively.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5382618&req=5

fig2: Mol­ecular packing in (I): (a) a view of the supra­molecular dimer sustained by N—H⋯S(thione) hydrogen bonds and (b) a view of the unit-cell contents shown in projection down the a axis. The N—H⋯S and C—H⋯π inter­actions are shown as orange and purple dashed lines, respectively.
Mentions: The most prominent feature of the mol­ecular packing is the formation of an eight-membered, centrosymmetric thio­amide synthon, {⋯HNCS}2 mediated by N—H⋯S(thione) hydrogen bonds, Fig. 2 ▸a and Table 1 ▸. The dimeric aggregates thus formed are connected into a three-dimensional architecture, Fig. 2 ▸b, via methyl­ene-C—H⋯π(tol­yl), tolyl-C—H⋯π(phen­yl) and phenyl-C—H⋯π(tol­yl) inter­actions, Table 1 ▸, indicating the tolyl ring accepts two such contacts. In essence, the C—H⋯π inter­actions connect mol­ecules into layers in the bc plane and these are linked by the N—H⋯S hydrogen bonds.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The title di­thio­carbazate ester (I), C18H18N2S2 [systematic name: (E)-4-methyl­benzyl 2-[(E)-3-phenyl­allyl­idene]hydrazinecarbodi­thio­ate, comprises an almost planar central CN2S2 residue [r.m.s. deviation = 0.0131 Å]. The methyl­ene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the mol­ecule approximates mirror symmetry with the 4-tolyl group bis­ected by the plane. The configuration about both double bonds in the N—N=C—C=C chain is E; the chain has an all trans conformation. In the crystal, eight-membered centrosymmetric thio­amide synthons, {⋯HNCS}2, are formed via N—H⋯S(thione) hydrogen bonds. Connections between the dimers via C—H⋯π inter­actions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an inter­action profile similar to that of a closely related analogue with an S-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connected via N—H⋯S hydrogen bonds is about 0.94 kcal mol−1 more stable than that in (I).

No MeSH data available.


Related in: MedlinePlus