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Crystal structure of (Z)-2-(5-fluoro-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide.

ABSTRACT: In the title compound, C9H7FN4OS, the mol-ecules are almost planar, with an r.m.s. deviation of 0.047?(3)?Å from the mean plane defined by the non-H atoms and a maximum deviation of 0.123?(2)?Å for the amine N atom. The torsion angle for the N-N-C-S unit is 176.57?(19)°. In the crystal, mol-ecules are linked into inversion dimers via pairs of N-H?F hydrogen bonds and, additionally, through N-H?O and N-H?S hydrogen bonds, building a two-dimensional hydrogen-bond network parallel to the (103) plane. An intra-molecular N-H?O inter-action is also observed.

SUBMITTER: Bittencourt VC

PROVIDER: S-EPMC4459295 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Crystal structure of (Z)-2-(5-fluoro-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide.

Bittencourt Viviane C D VC Almeida Vitor Y G VY Back Davi F DF Gervini Vanessa C VC de Oliveira Adriano Bof AB

Acta crystallographica. Section E, Crystallographic communications 20150509 Pt 6

In the title compound, C9H7FN4OS, the mol-ecules are almost planar, with an r.m.s. deviation of 0.047 (3) Å from the mean plane defined by the non-H atoms and a maximum deviation of 0.123 (2) Å for the amine N atom. The torsion angle for the N-N-C-S unit is 176.57 (19)°. In the crystal, mol-ecules are linked into inversion dimers via pairs of N-H⋯F hydrogen bonds and, additionally, through N-H⋯O and N-H⋯S hydrogen bonds, building a two-dimensional hydrogen-bond network parallel to the (103) plan ...[more]

PMID: 26090179

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2-(5-Chloro-2-oxoindolin-3-yl-idene)hydrazinecarbo-thio-amide.

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Hirshfeld analysis and mol-ecular docking with the RDR enzyme of 2-(5-chloro-2-oxoindolin-3-yl-idene)-N-methyl-hydrazinecarbo-thio-amide.

Project description:The acetic acid-catalyzed reaction between 5-chloro-isatin and 4-methyl-thio-semicarbazide yields the title compound, C10H9ClN4OS (I) (common name: 5-chloro-isatin-4-methyl-thio-semicarbazone). The mol-ecule is nearly planar (r.m.s. deviation = 0.047?Å for all non-H atoms), with a maximum deviation of 0.089?(1)?Å for the O atom. An S(6) ring motif formed by an intra-molecular N-H?O hydrogen bond is observed. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds, forming chains propagating along the a-axis direction. The chains are linked by N-H?S hydrogen bonds, forming a three-dimensional supra-molecular structure. The three-dimensional framework is reinforced by C-H?? inter-actions. The absolute structure of the mol-ecule in the crystal was determined by resonant scattering [Flack parameter = 0.006?(9)]. The crystal structure of the same compound, measured at 100?K, has been reported on previously [Qasem Ali et al. (2012 ?). Acta Cryst. E68, o964-o965]. The Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H?H (23.1%), H?C (18.4%), H?Cl (13.7%), H?S (12.0%) and H?O (11.3%) inter-actions. A mol-ecular docking evaluation of the title compound with the ribonucleoside diphosphate reductase (RDR) enzyme was carried out. The title compound (I) and the active site of the selected enzyme show Cl?H-C(LYS140), Cg(aromatic ring)?H-C(SER71), H?O-C(GLU200) and FeIII?O?FeIII inter-molecular inter-actions, which suggests a solid theoretical structure-activity relationship.

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