(E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide

The title compound, C17H15N3OS, crystallizes with two unique molecules, denoted 1 and 2, in the asymmetric unit. The two molecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both molecules adopt E configurations with respect to the C=N bonds. The...

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Main Authors: Ibrahim Baba, Jim Simpson, Yang Farina, Safa'a Faris Kayed
Format: Article
Language:English
Published: International Union of Crystallography 2011-10-01
Series:Acta Crystallographica Section E
Online Access:http://scripts.iucr.org/cgi-bin/paper?S1600536811037457
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spelling doaj-33a5e18688994442b034829a0c8a2a392020-11-25T02:15:05ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682011-10-016710o2687o268810.1107/S1600536811037457(E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamideIbrahim BabaJim SimpsonYang FarinaSafa'a Faris KayedThe title compound, C17H15N3OS, crystallizes with two unique molecules, denoted 1 and 2, in the asymmetric unit. The two molecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both molecules adopt E configurations with respect to the C=N bonds. The dihedral angles between the benzothiophene groups and N-bound phenyl rings are 36.36 (9)° for molecule 1 and 29.71 (9)° for molecule 2. The C=N—NH—C(O)NH ethylidene–hydrazinecarboxamide units are also reasonably planar, with r.m.s. deviations of 0.061 and 0.056 Å, respectively, for the two molecules. The methyl substituents lie 0.338 (3) and 0.396 (3) Å, respectively, from these planes. The C=N—NH—C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11)°, respectively, in molecules 1 and 2. This conformation is enhanced by weak intramolecular C—H...O hydrogen bonds between ortho-H atoms of the two phenyl rings and the carbonyl O atoms, which generate S(6) rings in each molecule. In the crystal, pairs of molecules are linked by pairs of intermolecular N—H...O hydrogen bonds into dimers. Alternating dimers are further interconnected by weak C—H...O contacts into zigzag rows along b. The rows are stacked along a by C—H...π contacts involving the benzene ring from molecule 2 and the thiophene ring from molecule 1 of adjacent benzothiophene units.http://scripts.iucr.org/cgi-bin/paper?S1600536811037457
collection DOAJ
language English
format Article
sources DOAJ
author Ibrahim Baba
Jim Simpson
Yang Farina
Safa'a Faris Kayed
spellingShingle Ibrahim Baba
Jim Simpson
Yang Farina
Safa'a Faris Kayed
(E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide
Acta Crystallographica Section E
author_facet Ibrahim Baba
Jim Simpson
Yang Farina
Safa'a Faris Kayed
author_sort Ibrahim Baba
title (E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide
title_short (E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide
title_full (E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide
title_fullStr (E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide
title_full_unstemmed (E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide
title_sort (e)-2-[1-(1-benzothiophen-2-yl)ethylidene]-n-phenylhydrazinecarboxamide
publisher International Union of Crystallography
series Acta Crystallographica Section E
issn 1600-5368
publishDate 2011-10-01
description The title compound, C17H15N3OS, crystallizes with two unique molecules, denoted 1 and 2, in the asymmetric unit. The two molecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both molecules adopt E configurations with respect to the C=N bonds. The dihedral angles between the benzothiophene groups and N-bound phenyl rings are 36.36 (9)° for molecule 1 and 29.71 (9)° for molecule 2. The C=N—NH—C(O)NH ethylidene–hydrazinecarboxamide units are also reasonably planar, with r.m.s. deviations of 0.061 and 0.056 Å, respectively, for the two molecules. The methyl substituents lie 0.338 (3) and 0.396 (3) Å, respectively, from these planes. The C=N—NH—C(O)NH planes are inclined to the phenyl rings at 13.65 (11) and 15.56 (11)°, respectively, in molecules 1 and 2. This conformation is enhanced by weak intramolecular C—H...O hydrogen bonds between ortho-H atoms of the two phenyl rings and the carbonyl O atoms, which generate S(6) rings in each molecule. In the crystal, pairs of molecules are linked by pairs of intermolecular N—H...O hydrogen bonds into dimers. Alternating dimers are further interconnected by weak C—H...O contacts into zigzag rows along b. The rows are stacked along a by C—H...π contacts involving the benzene ring from molecule 2 and the thiophene ring from molecule 1 of adjacent benzothiophene units.
url http://scripts.iucr.org/cgi-bin/paper?S1600536811037457
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AT yangfarina e211benzothiophen2ylethylidenenphenylhydrazinecarboxamide
AT safaafariskayed e211benzothiophen2ylethylidenenphenylhydrazinecarboxamide
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