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

doi:10.1107/S2056989015004958

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

Chemistry

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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 language	English
Pages (from-to)	o244-o245
Number of pages	2
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	71
Issue number	4
DOIs	https://doi.org/10.1107/S2056989015004958
Publication status	Published - 1 Apr 2015

Bibliographical note

Support for this project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS No. 9419400), Malaysian Fundamental Research Grant Scheme (FRGS No. 5524425) and the ScienceFund (Science Fund No. 5450726). We also thank Siti Khadijah Densabali for collecting the X-ray data. JJ wishes to acknowledge the Malaysian Government for sponsorship under the SGRA Scheme.

Keywords

Crystal structure
Hydrogen bonding
O - H⋯πinteractions
Thiosemicarbazide

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Crystal structure of 20-hydroxyacetophenone 4-methylthiosemicarbazide
© 2015 Jamsari et al. Licence: Creative Commons Attribution (CC-BY) https://creativecommons.org/licenses/by/4.0
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title = "Crystal structure of 2′-hydroxyaceto-phenone 4-methylthiosemicarbazide",

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.",

keywords = "Crystal structure, Hydrogen bonding, O - H⋯πinteractions, Thiosemicarbazide",

author = "Junita Jamsari and Abas, {Nur Fatihah} and Ravoof, {Thahira Begum S A} and Tiekink, {Edward R T} and Harrison, {W. T A}",

note = "Support for this project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS No. 9419400), Malaysian Fundamental Research Grant Scheme (FRGS No. 5524425) and the ScienceFund (Science Fund No. 5450726). We also thank Siti Khadijah Densabali for collecting the X-ray data. JJ wishes to acknowledge the Malaysian Government for sponsorship under the SGRA Scheme.",

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AU - Abas, Nur Fatihah

AU - Ravoof, Thahira Begum S A

AU - Tiekink, Edward R T

A2 - Harrison, W. T A

N1 - Support for this project came from Universiti Putra Malaysia (UPM) under their Research University Grant Scheme (RUGS No. 9419400), Malaysian Fundamental Research Grant Scheme (FRGS No. 5524425) and the ScienceFund (Science Fund No. 5450726). We also thank Siti Khadijah Densabali for collecting the X-ray data. JJ wishes to acknowledge the Malaysian Government for sponsorship under the SGRA Scheme.

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N2 - 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.

AB - 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.

KW - Crystal structure

KW - Hydrogen bonding

KW - O - H⋯πinteractions

KW - Thiosemicarbazide

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JF - Acta Crystallographica Section E: Structure Reports Online

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

Abstract

Bibliographical note

Keywords

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