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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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Relative percentage contributions of close contacts to the Hirshfeld surfaces of (I) and (II).
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fig3: Relative percentage contributions of close contacts to the Hirshfeld surfaces of (I) and (II).

Mentions: Both (I) and (II) exhibit closely related topological inter­actions as evidenced by the relative distribution of similar contacts, Fig. 3 ▸, computed based upon the mapping of the contact distances at specific points on their Hirshfeld surfaces (Spackman & Jayatilaka, 2009 ▸). Among the inter­actions, H⋯H contacts constitute the most dominant contacts in (I) and (II) at approximately 46.2 and 45.4%, respectively. This is followed by C⋯H/H⋯C [ca 25.4% for (I) and 23.8% for (II)], S⋯H/H⋯S [ca 17.5 and 16.9%], N⋯H/H⋯N [ca 5.6 and 5.5%] as well as other minor inter­actions including N⋯C/C⋯N, S⋯C/C⋯S and S⋯N/N⋯S, which constitute less than 5% of the overall contacts.


A cinnamaldehyde Schiff base of S -(4-methyl ­ benz ­ yl) di ­ thio ­ carbazate: crystal structure, Hirshfeld surface analysis and computational study
Relative percentage contributions of close contacts to the Hirshfeld surfaces of (I) and (II).
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig3: Relative percentage contributions of close contacts to the Hirshfeld surfaces of (I) and (II).
Mentions: Both (I) and (II) exhibit closely related topological inter­actions as evidenced by the relative distribution of similar contacts, Fig. 3 ▸, computed based upon the mapping of the contact distances at specific points on their Hirshfeld surfaces (Spackman & Jayatilaka, 2009 ▸). Among the inter­actions, H⋯H contacts constitute the most dominant contacts in (I) and (II) at approximately 46.2 and 45.4%, respectively. This is followed by C⋯H/H⋯C [ca 25.4% for (I) and 23.8% for (II)], S⋯H/H⋯S [ca 17.5 and 16.9%], N⋯H/H⋯N [ca 5.6 and 5.5%] as well as other minor inter­actions including N⋯C/C⋯N, S⋯C/C⋯S and S⋯N/N⋯S, which constitute less than 5% of the overall contacts.

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.