Crystal structure of 2′-hydroxyaceto-phenone 4-methylthiosemicarbazide

Junita Jamsari, Nur Fatihah Abas, Thahira Begum S A Ravoof*, Edward R T Tiekink, W. T A Harrison (Editor)

*Corresponding author for this work

Research output: Contribution to journalArticle

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Abstract

In the organic molecule of the title hydrate, C11H15N3OS·H2O, {systematic name: 3-ethyl-1-{(E)-[1-(2-hydroxyphenyl) ethyl-idene]amino}thiourea monohydrate}, a dihedral angle of 5.39 (2)° is formed between the hydroxybenzene ring and the non-H atoms comprising the side chain (r.m.s. deviation = 0.0625 Å), with the major deviation from planarity noted for the terminal ethyl group [the C - N - C - C torsion angle = - 172.17 (13)°]. The N - H H atoms are syn and an intramolecular hydroxy-imine O - H⋯N hydrogen bond is noted. In the crystal, the N-bonded H atoms form hydrogen bonds to symmetry-related water molecules, and the latter form donor interactions with the hydroxy O atom and with a hydroxybenzene ring, forming a O - H⋯π interaction. The hydrogen bonding leads to supramolecular tubes aligned along the b axis. The tubes are connected into layers via C - H⋯O interactions, and these stack along the c axis with no directional interactions between them.

Original languageEnglish
Pages (from-to)o244-o245
Number of pages2
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number4
DOIs
Publication statusPublished - 1 Apr 2015

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Crystal structure
Atoms
Hydrogen bonds
crystal structure
Phenol
atoms
interactions
hydrogen bonds
tubes
deviation
Thiourea
Molecules
Imines
Thioureas
rings
thioureas
Dihedral angle
Hydrates
hydrates
Torsional stress

Keywords

  • Crystal structure
  • Hydrogen bonding
  • O - H⋯πinteractions
  • Thiosemicarbazide

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

Crystal structure of 2′-hydroxyaceto-phenone 4-methylthiosemicarbazide. / Jamsari, Junita; Abas, Nur Fatihah; Ravoof, Thahira Begum S A; Tiekink, Edward R T; Harrison, W. T A (Editor).

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 71, No. 4, 01.04.2015, p. o244-o245.

Research output: Contribution to journalArticle

Jamsari, Junita ; Abas, Nur Fatihah ; Ravoof, Thahira Begum S A ; Tiekink, Edward R T ; Harrison, W. T A (Editor). / Crystal structure of 2′-hydroxyaceto-phenone 4-methylthiosemicarbazide. In: Acta Crystallographica Section E: Structure Reports Online. 2015 ; Vol. 71, No. 4. pp. o244-o245.
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abstract = "In the organic molecule of the title hydrate, C11H15N3OS·H2O, {systematic name: 3-ethyl-1-{(E)-[1-(2-hydroxyphenyl) ethyl-idene]amino}thiourea monohydrate}, a dihedral angle of 5.39 (2)° is formed between the hydroxybenzene ring and the non-H atoms comprising the side chain (r.m.s. deviation = 0.0625 {\AA}), with the major deviation from planarity noted for the terminal ethyl group [the C - N - C - C torsion angle = - 172.17 (13)°]. The N - H H atoms are syn and an intramolecular hydroxy-imine O - H⋯N hydrogen bond is noted. In the crystal, the N-bonded H atoms form hydrogen bonds to symmetry-related water molecules, and the latter form donor interactions with the hydroxy O atom and with a hydroxybenzene ring, forming a O - H⋯π interaction. The hydrogen bonding leads to supramolecular tubes aligned along the b axis. The tubes are connected into layers via C - H⋯O interactions, and these stack along the c axis with no directional interactions between them.",
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