(E)-1-(2,5-Dichlorothiophen-3-yl)ethan-one [8-(trifluoromethyl)quinolin-4- yl]hydrazone

A. S. Dayananda, H. S. Yathirajan*, William Thomas Alexander Harrison, Alexandra M Z Slawin

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

In the title compound, C 16H 10Cl 2F 3N 3S, the dihedral angle between the quinoline and thio-phene ring systems is 4.94 (10)°. The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thio-phene ring takes part in weak π-π stacking inter-actions with the pyridine ring [centroid-to-centroid separation = 3.7553 (19) Å and inter-planar angle = 5.48 (12)°] and the benzene ring [3.7927 (19) Å and 4.58 (12)°]. Together, these lead to [100] stacks of mol-ecules in an alternating head-to-tail arrangement, with two π-π stacking contacts between each adjacent pair.

Original languageEnglish
Article number7
JournalActa Crystallographica Section E: Structure Reports Online
Volume68
Issue number3
Early online dateMar 2012
DOIs
Publication statusPublished - Mar 2012

Fingerprint

Hydrazones
hydrazones
quinoline
Dihedral angle
Benzene
Pyridine
Hydrogen bonds
Crystals
rings
centroids
crowding
dihedral angle
pyridines
benzene
hydrogen bonds
pyridine
crystals

Keywords

  • data-to-parameter ratio = 12.5
  • mean σ(C-C) = 0.004 Å
  • R factor = 0.049
  • single-crystal X-ray study
  • T = 73 K
  • wR factor = 0.128

ASJC Scopus subject areas

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

Cite this

(E)-1-(2,5-Dichlorothiophen-3-yl)ethan-one [8-(trifluoromethyl)quinolin-4- yl]hydrazone. / Dayananda, A. S.; Yathirajan, H. S.; Harrison, William Thomas Alexander; Slawin, Alexandra M Z.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 68, No. 3, 7, 03.2012.

Research output: Contribution to journalArticle

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abstract = "In the title compound, C 16H 10Cl 2F 3N 3S, the dihedral angle between the quinoline and thio-phene ring systems is 4.94 (10)°. The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thio-phene ring takes part in weak π-π stacking inter-actions with the pyridine ring [centroid-to-centroid separation = 3.7553 (19) {\AA} and inter-planar angle = 5.48 (12)°] and the benzene ring [3.7927 (19) {\AA} and 4.58 (12)°]. Together, these lead to [100] stacks of mol-ecules in an alternating head-to-tail arrangement, with two π-π stacking contacts between each adjacent pair.",
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AU - Dayananda, A. S.

AU - Yathirajan, H. S.

AU - Harrison, William Thomas Alexander

AU - Slawin, Alexandra M Z

PY - 2012/3

Y1 - 2012/3

N2 - In the title compound, C 16H 10Cl 2F 3N 3S, the dihedral angle between the quinoline and thio-phene ring systems is 4.94 (10)°. The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thio-phene ring takes part in weak π-π stacking inter-actions with the pyridine ring [centroid-to-centroid separation = 3.7553 (19) Å and inter-planar angle = 5.48 (12)°] and the benzene ring [3.7927 (19) Å and 4.58 (12)°]. Together, these lead to [100] stacks of mol-ecules in an alternating head-to-tail arrangement, with two π-π stacking contacts between each adjacent pair.

AB - In the title compound, C 16H 10Cl 2F 3N 3S, the dihedral angle between the quinoline and thio-phene ring systems is 4.94 (10)°. The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thio-phene ring takes part in weak π-π stacking inter-actions with the pyridine ring [centroid-to-centroid separation = 3.7553 (19) Å and inter-planar angle = 5.48 (12)°] and the benzene ring [3.7927 (19) Å and 4.58 (12)°]. Together, these lead to [100] stacks of mol-ecules in an alternating head-to-tail arrangement, with two π-π stacking contacts between each adjacent pair.

KW - data-to-parameter ratio = 12.5

KW - mean σ(C-C) = 0.004 Å

KW - R factor = 0.049

KW - single-crystal X-ray study

KW - T = 73 K

KW - wR factor = 0.128

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DO - 10.1107/S1600536812005673

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JO - Acta Crystallographica Section E: Structure Reports Online

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SN - 1600-5368

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