(E)-3,4-Dihydroxy-benzaldehyde 4-ethyl-thio-semicarbazone

Safa'a Fares Kayed, Yang Farina Abdul Aziz, Ibrahim Baba, Jim Simpson

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The title compound, C10H13N3O2S, was prepared by condensation of 3,4-dihydroxy-benzaldehyde with 4-ethyl-3-thio-semicarbazide. The mol-ecule adopts an E configuration with respect to the C=N bond. One of the OH substituents on the dihydroxy-benzene ring is disordered over the two possible 3-positions on either side of the ordered 4-hydr-oxy group. The occupancy of the major disorder component refined to 0.633 (7). The mol-ecule is essentially planar, with an r.m.s. deviation through all non-H atoms of 0.0862 Å. An intra-molecular N - H⋯N hydrogen bond forms between the outer amine residue and the imine N atom, generating an S(5) ring motif and contributing to the planarity of the mol-ecule. In the crystal structure, an extensive network of classical O - H⋯O, O - H⋯S and N - H⋯S hydrogen bonds and weak C - H⋯O and S⋯O [3.301 (3) Å] inter-actions link mol-ecules into sheets running approximately parallel to the ab plane.

Original languageEnglish
JournalActa Crystallographica Section E: Structure Reports Online
Volume64
Issue number5
DOIs
Publication statusPublished - 30 Apr 2008

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Semicarbazones
Hydrogen
Hydrogen bonds
hydrogen bonds
Atoms
Imines
rings
Benzene
imines
Amines
atoms
Condensation
amines
condensation
Crystal structure
benzene
disorders
deviation
crystal structure
configurations

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Structural Biology

Cite this

(E)-3,4-Dihydroxy-benzaldehyde 4-ethyl-thio-semicarbazone. / Kayed, Safa'a Fares; Abdul Aziz, Yang Farina; Baba, Ibrahim; Simpson, Jim.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 64, No. 5, 30.04.2008.

Research output: Contribution to journalArticle

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N2 - The title compound, C10H13N3O2S, was prepared by condensation of 3,4-dihydroxy-benzaldehyde with 4-ethyl-3-thio-semicarbazide. The mol-ecule adopts an E configuration with respect to the C=N bond. One of the OH substituents on the dihydroxy-benzene ring is disordered over the two possible 3-positions on either side of the ordered 4-hydr-oxy group. The occupancy of the major disorder component refined to 0.633 (7). The mol-ecule is essentially planar, with an r.m.s. deviation through all non-H atoms of 0.0862 Å. An intra-molecular N - H⋯N hydrogen bond forms between the outer amine residue and the imine N atom, generating an S(5) ring motif and contributing to the planarity of the mol-ecule. In the crystal structure, an extensive network of classical O - H⋯O, O - H⋯S and N - H⋯S hydrogen bonds and weak C - H⋯O and S⋯O [3.301 (3) Å] inter-actions link mol-ecules into sheets running approximately parallel to the ab plane.

AB - The title compound, C10H13N3O2S, was prepared by condensation of 3,4-dihydroxy-benzaldehyde with 4-ethyl-3-thio-semicarbazide. The mol-ecule adopts an E configuration with respect to the C=N bond. One of the OH substituents on the dihydroxy-benzene ring is disordered over the two possible 3-positions on either side of the ordered 4-hydr-oxy group. The occupancy of the major disorder component refined to 0.633 (7). The mol-ecule is essentially planar, with an r.m.s. deviation through all non-H atoms of 0.0862 Å. An intra-molecular N - H⋯N hydrogen bond forms between the outer amine residue and the imine N atom, generating an S(5) ring motif and contributing to the planarity of the mol-ecule. In the crystal structure, an extensive network of classical O - H⋯O, O - H⋯S and N - H⋯S hydrogen bonds and weak C - H⋯O and S⋯O [3.301 (3) Å] inter-actions link mol-ecules into sheets running approximately parallel to the ab plane.

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