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Crystal structures of 2-[5-nitrothien-2-yl)- CH=N–NR–CO(CH2)n]thiophene compounds (R = H or Me; n = 0 or 1)

  • Laura N.F. Cardoso , Thais C.M. Noguiera , Carlos R. Kaiser , James L. Wardell EMAIL logo , Solange M.S.V. Wardell and Marcus V.N. de Souza
Published/Copyright: December 16, 2015
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 231 Issue 3

Abstract

The crystal structures of four acylhydrazonyl derivatives of thiophene, 2-(ArCH=N–NHCO)- thiophene, (1a), 2-(ArCH=N–NMeCO)-thiophene, (2a), 2-(ArCH=N–NHCOCH2)-thiophene, (3a) and 2-(ArCH= N–NMeCOCH2)-thiophene, (4a) [in each case Ar= 5-nitrothien-2-yl] are reported. The molecular conformations of 1a and 2a are near planar, while those of 3a and 4a exhibit bends at the methylene carbon. Methylations at the hydrazonyl groups in 1a and 3a, to give 2a and 4a, do not result in any significant changes in the molecular conformations. Each of the four molecular conformations possesses a ZC(O)NR/E(C=N) arrangement about the C(O)–NR–N=C(H, aryl) fragment (R=H or Me). The dominant intermolecular interactions in 1a and 3a are N–H···O(carbonyl) hydrogen bonds, with other intermolecular interactions being weaker interactions: C–H···O and N–O···π in 1a and C–H···X (X=O, S, π) and π–π interactions in 3a. In the N-methylated compounds, the intermolecular interactions are restricted to weaker C–H···O hydrogen bonds in 2a and C–H···X (X=O or π) interactions in 4a.

Keywords: acyl hydrazones; crystal structures; thienyl derivatives
Corresponding author: James L. Wardell, Fundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos-Far Manguinhos, Manguinhos, 21041-250, Rio de Janeiro, Brazil; and Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, E-mail:

Acknowledgments

The use of the NCS crystallographic service at Southampton and the valuable assistance of the staff there are gratefully acknowledged. JLW thanks FAPERJ and CNPq, Brazil for support.

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Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2015-1902) offers supplementary material, available to authorized users.

Received: 2015-10-5
Accepted: 2015-11-17
Published Online: 2015-12-16
Published in Print: 2016-3-1

©2016 by De Gruyter

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https://doi.org/10.1515/zkri-2015-1902
Keywords for this article
acyl hydrazones; crystal structures; thienyl derivatives

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. SrPt2Al2 – A (3+2)D-incommensurately modulated variant of the CaBe2Ge2 type structure
  5. The modulated structure of intermediate-valent CeCoGa
  6. Organic and Metalorganic Crystal Structures
  7. Serendipitous compositional and structural diversity in urotropine adducts of binary cadmium xanthates
  8. Crystal structures of 2-[5-nitrothien-2-yl)- CH=N–NR–CO(CH2)n]thiophene compounds (R = H or Me; n = 0 or 1)
  9. Molecular structure studies of novel bronchodilatory-active 4-azafluorenes
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