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Crystal structures and vibrational spectra of biuret co-crystals with cyanuric and glutaric acids, discussion of hydrogen bonding involving carbonyl groups

  • Irena Matulková , Jana Mathauserová , Ivana Císařová , Ivan Němec and Jan Fábry EMAIL logo
Published/Copyright: March 23, 2016
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 231 Issue 5

Abstract

The title structures of biuret-cyanuric acid (2/2) monohydrate, C10H18N12O11, 1 [P1̅, Z=2, a=8.2598(4) Å, b=10.8795(5) Å, c=11.9138(6) Å, α=67.036(1)°, β= 79.842(2)°, γ=69.859(2)°, V=924.38(8) Å3], and of biuret-glutaric acid (1/1), C7H13N3O6, 2 [P1̅, Z=2, a=5.0044(3) Å, b=7.0832(3) Å, c=14.9803(10) Å, α=102.860(4)°, β= 91.899(3)°, γ=102.202(4)°, V=504.20(5) Å3], show usual features both in constitution and intermolecular contacts except for a slightly longer C=O bond length in one of the carbonyl groups in 2. The biuret molecules have conformations with anti-parallel arrangement of the carbonyl groups. In each structure O–H…O and N–H…O hydrogen bonds of the moderate strength are present. The new results are compared with other structures which contain biuret molecules. The influence of the hydrogen bonding on the bond length of the carbonyl group C=O in the fragment NH2-(C=O)-NH with amine and hydroxyl donors has also been investigated. It transpires that the C=O…H angle of about 120° favors a slight elongation of the C=O bond length. The elongation of the C=O bond is more susceptible to the relative orientation of the C=O group with regard to amine over hydroxyl groups. This is the likely explanation why one of the C=O bonds in 2 is slightly longer than usual because this carbonyl group is simultaneously involved in two hydrogen bonds where C=O…H–O and C=O…H–N satisfy the 120° condition. Vibrational spectra of the title structures were also recorded and assigned.

Keywords: biuret; crystal structure analysis; hydrogen bonding; vibrational spectroscopy; X-ray diffraction
Corresponding author: Jan Fábry, Institute of Physics, Academy of Sciences of the Czech Republic, Na Slovance 2, 182 21 Praha 8, Czech Republic, E-mail:

Acknowledgments

This work was supported by the Czech Science Foundation (grant no. 14-05506S).

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Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2015-1901) offers supplementary material, available to authorized users.

Received: 2015-9-29
Accepted: 2016-2-10
Published Online: 2016-3-23
Published in Print: 2016-5-1

©2016 by De Gruyter

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. β-K2Se2 and K2Se4: missing links in the binary system K-Se
  5. Debye function analysis of nanocrystalline gallium oxide γ-Ga2O3
  6. Crystal structure of the alluaudite Ag2Mn3(VO4)3
  7. Organic and Metalorganic Crystal Structures
  8. Crystal structures of (E)-2-((2-((pyridin-2-yl)hydrazonyl)methyl)phenolic compounds: different sets of classical hydrogen bonds, X–H···Y (X, Y = O, N)
  9. Syntheses, crystal structures and thermal properties of two novel isostructural Co(III) complexes with salophen ligand
  10. Crystal structures and vibrational spectra of biuret co-crystals with cyanuric and glutaric acids, discussion of hydrogen bonding involving carbonyl groups
  11. Crystallographic Computing
  12. Discontinuous modulation functions and their application for analysis of modulated structures with the computing system JANA2006
  13. Corrigendum
  14. Corrigendum to: Disorder, pseudo symmetry and photoluminescence properties of a new diphosphate K2Ba3(P2O7)2
https://doi.org/10.1515/zkri-2015-1901
Keywords for this article
biuret; crystal structure analysis; hydrogen bonding; vibrational spectroscopy; X-ray diffraction

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. β-K2Se2 and K2Se4: missing links in the binary system K-Se
  5. Debye function analysis of nanocrystalline gallium oxide γ-Ga2O3
  6. Crystal structure of the alluaudite Ag2Mn3(VO4)3
  7. Organic and Metalorganic Crystal Structures
  8. Crystal structures of (E)-2-((2-((pyridin-2-yl)hydrazonyl)methyl)phenolic compounds: different sets of classical hydrogen bonds, X–H···Y (X, Y = O, N)
  9. Syntheses, crystal structures and thermal properties of two novel isostructural Co(III) complexes with salophen ligand
  10. Crystal structures and vibrational spectra of biuret co-crystals with cyanuric and glutaric acids, discussion of hydrogen bonding involving carbonyl groups
  11. Crystallographic Computing
  12. Discontinuous modulation functions and their application for analysis of modulated structures with the computing system JANA2006
  13. Corrigendum
  14. Corrigendum to: Disorder, pseudo symmetry and photoluminescence properties of a new diphosphate K2Ba3(P2O7)2
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