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

Safa'A Faris Kayed, Yang Farina Abdul Aziz, Jim Simpson, Ibrahim Baba

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The title compound, C 17H 15N 3OS, crystallizes with two unique mol-ecules, denoted 1 and 2, in the asymmetric unit. The two mol-ecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both mol-ecules 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 mol-ecule 1 and 29.71 (9)° for mol-ecule 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 mol-ecules. 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 mol-ecules 1 and 2. This conformation is enhanced by weak intra-molecular 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 mol-ecule. In the crystal, pairs of mol-ecules are linked by pairs of inter-molecular N-H⋯O hydrogen bonds into dimers. Alternating dimers are further inter-connected 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.

Original languageEnglish
JournalActa Crystallographica Section E: Structure Reports Online
Volume67
Issue number10
DOIs
Publication statusPublished - Oct 2011

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Dimers
Hydrogen bonds
Thiophenes
Atoms
Molecules
rings
Thiophene
Dihedral angle
Benzene
Conformations
Crystals
dimers
hydrogen bonds
deviation
thiophenes
atoms
dihedral angle
benzothiophene
molecules
benzene

Keywords

  • data-to-parameter ratio = 21.0
  • mean σ(C-C) = 0.003 Å
  • R factor =0.054
  • single-crystal X-ray study
  • T = 89 K
  • wR factor = 0.147

ASJC Scopus subject areas

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

Cite this

(E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide. / Kayed, Safa'A Faris; Abdul Aziz, Yang Farina; Simpson, Jim; Baba, Ibrahim.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 67, No. 10, 10.2011.

Research output: Contribution to journalArticle

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abstract = "The title compound, C 17H 15N 3OS, crystallizes with two unique mol-ecules, denoted 1 and 2, in the asymmetric unit. The two mol-ecules are closely similar and overlay with an r.m.s. deviation of 0.053 {\AA}. Both mol-ecules 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 mol-ecule 1 and 29.71 (9)° for mol-ecule 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 {\AA}, respectively, for the two mol-ecules. The methyl substituents lie 0.338 (3) and 0.396 (3) {\AA}, 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 mol-ecules 1 and 2. This conformation is enhanced by weak intra-molecular 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 mol-ecule. In the crystal, pairs of mol-ecules are linked by pairs of inter-molecular N-H⋯O hydrogen bonds into dimers. Alternating dimers are further inter-connected 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.",
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T1 - (E)-2-[1-(1-Benzothiophen-2-yl)ethylidene]-N-phenylhydrazinecarboxamide

AU - Kayed, Safa'A Faris

AU - Abdul Aziz, Yang Farina

AU - Simpson, Jim

AU - Baba, Ibrahim

PY - 2011/10

Y1 - 2011/10

N2 - The title compound, C 17H 15N 3OS, crystallizes with two unique mol-ecules, denoted 1 and 2, in the asymmetric unit. The two mol-ecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both mol-ecules 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 mol-ecule 1 and 29.71 (9)° for mol-ecule 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 mol-ecules. 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 mol-ecules 1 and 2. This conformation is enhanced by weak intra-molecular 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 mol-ecule. In the crystal, pairs of mol-ecules are linked by pairs of inter-molecular N-H⋯O hydrogen bonds into dimers. Alternating dimers are further inter-connected 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.

AB - The title compound, C 17H 15N 3OS, crystallizes with two unique mol-ecules, denoted 1 and 2, in the asymmetric unit. The two mol-ecules are closely similar and overlay with an r.m.s. deviation of 0.053 Å. Both mol-ecules 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 mol-ecule 1 and 29.71 (9)° for mol-ecule 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 mol-ecules. 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 mol-ecules 1 and 2. This conformation is enhanced by weak intra-molecular 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 mol-ecule. In the crystal, pairs of mol-ecules are linked by pairs of inter-molecular N-H⋯O hydrogen bonds into dimers. Alternating dimers are further inter-connected 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.

KW - data-to-parameter ratio = 21.0

KW - mean σ(C-C) = 0.003 Å

KW - R factor =0.054

KW - single-crystal X-ray study

KW - T = 89 K

KW - wR factor = 0.147

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U2 - 10.1107/S1600536811037457

DO - 10.1107/S1600536811037457

M3 - Article

VL - 67

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

IS - 10

ER -