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Crystal structures and Hirshfeld surface analyses of halogen substituted azine derivatives, 1,4-bis(halophenyl)-2,3-diazabuta-1,3-dienes

  • Nathasha R. de L Correira , Thais C.M. Noguiera , Alessandra C. Pinheiro , Marcus V.N. de Souza , Ligia R. Gomes , John N. Low , James L. Wardell EMAIL logo and Solange M.S.V. Wardell
Published/Copyright: October 18, 2017
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 233 Issue 2

Abstract

The crystal structures and Hirshfeld surface analyses are reported, from data collected at 100 K, of six 1,4-bis(X,Y-phenyl)-2,3-diazabuta-1,3-dienes (1–6), namely (1: X, Y=H, 4-Cl; 2: X, Y=3,4-Cl2; 3: X, Y=2,4-Cl2; 4: X, Y=H, 2-Br, H; 5: X, Y=H, 3-Br; 6: X, Y=H, 4-Br. The six halogen derivatives crystallise in the monoclinic group P21/c. In each case, the asymmetric unit is one half of the molecule, with the molecules lying across inversion centres, midway between the N–N bonds, with the central C–C=N–N=C–C fragments having all transoid conformations. Each of the six molecules deviates a little from overall planarity. The π···π stacking interactions are the most important intermolecular interactions in each of the six compounds. In the cases of 3 and 4, the π···π stacks are augmented by additional C–X···π (X=Cl or Br) interactions, while in 4, the π···π stacks are linked by weak Br···Br interactions, and in 3, weak Cl···Cl contacts are considered to be also involved in cementing the supra molecular arrangements. The short separations of the layers within the stacks and the extent of the overlaps of the π systems point to significant strengths of the π···π interactions. Comparisons with published structures of related chloro and fluoro compounds indicated similar results: related iodo derivatives, IC6H4CH=N–N=CHC6H4I do not possess as strong π···π interactions. The Hirshfeld analysis indicated further intermolecular contacts which fell outside the normal PLATON cutoff values.

Keywords: azines; crystal structures; Hirshfeld surface analysis; π···π stacks

Acknowledgments

The authors thank the National Crystallographic Service, University of Southampton for the data collection, and for their help and advice. This work was supported by the Portuguese Foundation for Science and Technology (FCT) UID/Multi/04546/2013, and by CAPES (Brazil).

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Supplemental Material:

The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2017-2081).

Received: 2017-6-4
Accepted: 2017-8-31
Published Online: 2017-10-18
Published in Print: 2018-2-23

©2018 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

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  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Syntheses, crystal structures and photoluminescence properties of two rare-earth molybdates CsLn(MoO4)2 (Ln=Eu, Tb)
  5. Two superstructures of Ce3Rh4Ge4
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  8. Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes
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  10. Crystal structures and Hirshfeld surface analyses of halogen substituted azine derivatives, 1,4-bis(halophenyl)-2,3-diazabuta-1,3-dienes
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https://doi.org/10.1515/zkri-2017-2081
Keywords for this article
azines; crystal structures; Hirshfeld surface analysis; π···π stacks

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Syntheses, crystal structures and photoluminescence properties of two rare-earth molybdates CsLn(MoO4)2 (Ln=Eu, Tb)
  5. Two superstructures of Ce3Rh4Ge4
  6. Organic and Metalorganic Crystal Structures
  7. Organic-inorganic hybrid materials from divalent metal cations and expanded N,N′-donor linkers
  8. Crystallographic and docking (Cathepsins B, K, L and S) studies on bioactive halotelluroxetanes
  9. Radical scavenging potency of 2-(benzofuran-2-yl)-2-oxoethyl 3-(methyl/amino)benzoate: synthesis, crystal structure and Hirshfeld surface analysis
  10. Crystal structures and Hirshfeld surface analyses of halogen substituted azine derivatives, 1,4-bis(halophenyl)-2,3-diazabuta-1,3-dienes
  11. Proton-transfer compounds featuring the unusual 4-arsonoanilinium cation from the reaction of (4-aminophenyl)arsonic acid with strong organic acids
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