Salian, Akshatha R. ; Foro, Sabine ; Thimme Gowda, B. (2018)
Crystal structure and Hirshfeld surface analysis of (E)-N′-benzylidene-4-chlorobenzenesulfonohydrazide and of its (E)-4-chloro-N′-(ortho- and para-methylbenzylidene)benzenesulfonohydrazide derivatives.
In: Acta Crystallographica Section E Crystallographic Communications, 74 (11)
doi: 10.1107/S2056989018014500
Artikel, Bibliographie

Kurzbeschreibung (Abstract)

(E)-N'-Benzylidene-4-chlorobenzenesulfonohydrazide, C13H11ClN2O2S, (I), and its ortho- and para-methylsubstituted derivatives, C14H13ClN2O2S, namely (E)-4-chloro-N'-(2-methylbenzylidene)benzenesulfonohydrazide, (II), and (E)-4-chloro-N'-(4-methylbenzylidene)benzenesulfonohydrazide, (III), have been synthesized, characterized spectroscopically and their crystal structures determined to investigate the effect of the substitution site of the benzylidene group on the structural and supramolecular features in these compounds. Compounds (I) and (II) are isotypic while compound (III) is different. All three molecules are bent at the S atom with C-S-N-N torsion angles of -66.0 (3), -66.0 (3) and -58.4 (2)degrees for (I), (II) and (III), respectively. The hydrazone portions of the molecules, S-N-N=C, are slightly twisted from planarity, with a torsion angle of 166.5 (3)degrees in (I), 165.4 (3)degrees in (II) and 157.9 (2)degrees in (III). The two aromatic rings present in the compounds are inclined to each other by 78.4 (2), 74.8 (2) and 76.9 (1)degrees in (I), (II) and (III), respectively. In the crystal structure of the parent compound (I), and of the ortho-methyl derivative (II), an N-H center dot center dot center dot O hydrogen bond links the molecules into chains along [001], which are interconnected by weak intermolecular C-H center dot center dot center dot O interactions, generating layers lying parallel to the bc plane. In the crystal of the para derivative (III), however, the packing is significantly different. Here molecules are linked by pairs of N-H center dot center dot center dot O hydrogen bonds, forming inversion dimers with an R-2(2)(8) ring motif. The dimers are then linked by C-Cl center dot center dot center dot pi interactions, forming ribbons propagating along [1 (1) over bar0]. Hirshfeld surface analyses show that the van der Waals interactions constitute the major contribution to the intermolecular interactions in the crystal structures of all three compounds. The fingerprint plots indicate that the H center dot center dot center dot H contacts make the largest contributions to the Hirshfeld surfaces.

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