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Crystal structure and Hirshfeld surface analysis of (Z)-4-chloro-N'-(4-oxo-thia-zol-idin-2-yl-idene)benzene-sulfono-hydrazide monohydrate.

ABSTRACT: The asymmetric unit of the title thia-zole derivative containing a sulfonyl-hydrazinic moiety, C₉H₈ClN₃O₃S₂·H₂O, consists of two independent mol-ecules and two water mol-ecules. The central parts of the mol-ecules are twisted as both the mol-ecules are bent at both the S and N atoms. In the crystal, N-H⋯N, N-H⋯O, C-H⋯O and O-H⋯O hydrogen-bonding inter-actions connect the mol-ecules, forming layers parallel to the ab plane. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from O⋯H/H⋯O (32.9%) and H⋯H (22.6%) inter-actions.

SUBMITTER: Pai N

PROVIDER: S-EPMC6218911 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:(E)-N'-Benzyl-idene-4-chloro-benzene-sulfono-hydrazide, C13H11ClN2O2S, (I), and its ortho- and para-methyl-substituted derivatives, C14H13ClN2O2S, namely (E)-4-chloro-N'-(2-methyl-benzyl-idene)benzene-sulfono-hydrazide, (II), and (E)-4-chloro-N'-(4-methyl-benzyl-idene)benzene-sulfono-hydrazide, (III), have been synthesized, characterized spectroscopically and their crystal structures determined to investigate the effect of the substitution site of the benzyl-idene group on the structural and supra-molecular features in these compounds. Compounds (I) and (II) are isotypic while compound (III) is different. All three mol-ecules are bent at the S atom with C-S-N-N torsion angles of -66.0 (3), -66.0 (3) and -58.4 (2)° for (I), (II) and (III), respectively. The hydrazone portions of the mol-ecules, S-N-N=C, are slightly twisted from planarity, with a torsion angle of 166.5 (3)° in (I), 165.4 (3)° in (II) and 157.9 (2)° 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)° 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⋯O hydrogen bond links the mol-ecules into chains along [001], which are inter-connected by weak inter-molecular C-H⋯O inter-actions, generating layers lying parallel to the bc plane. In the crystal of the para derivative (III), however, the packing is significantly different. Here mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(8) ring motif. The dimers are then linked by C-Cl⋯π inter-actions, forming ribbons propagating along [10]. Hirshfeld surface analyses show that the van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions in the crystal structures of all three compounds. The fingerprint plots indicate that the H⋯H contacts make the largest contributions to the Hirshfeld surfaces.

Dataset Information

Crystal structure and Hirshfeld surface analysis of (Z)-4-chloro-N'-(4-oxo-thia-zol-idin-2-yl-idene)benzene-sulfono-hydrazide monohydrate.

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