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Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate

  • Christiana Bamigboye , Hanna S. Abbo , Huey Chong Kwong , Sang Loon Tan , Edward R.T. Tiekink EMAIL logo , Fadhil S. Kamounah and Salam J.J. Titinchi EMAIL logo
Published/Copyright: June 14, 2021
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 236 Issue 5-7

Abstract

X-ray crystallography on [EtOC(=O)N(H)C(=N+H2)NH2]Cl·½H2O (1) shows the asymmetric unit to comprise two independent cations, two chloride anions and crystal water. The main conformational difference between the cations is seen in the relative orientation of the ethyl groups; geometry-optimisation confirms the all-trans conformation is the most stable. The remaining parts of the cations are co-planar and feature intramolecular N–H···O(carbonyl) hydrogen bonds. An analysis of the C–N bonds suggests substantial delocalisation of the positive charge over the CN3 atoms. In the crystal, columns comprising the first independent cation are surrounded by four columns of the second cation within a network of water-O–H···Cl, N–H···Cl and N–H···O(water, carbonyl) hydrogen bonds, many of which are charge-assisted. The packing has been further investigated by Hirshfeld surface analysis, molecular electrostatic potential and interaction energy calculations. The charge-assisted N–H···Cl hydrogen bonds are significantly stronger than the water-O–H···Cl interactions consistent the distribution of the positive charge over the CN3 atoms.

Keywords: carbamate; computational chemistry; crystal structure analysis; dicyandiamide; Hirshfeld analysis; hydrogen bonding
Corresponding authors: Salam J.J. Titinchi, Department of Chemistry, University of the Western Cape, Cape Town, South Africa, E-mail: ; and Edward R.T. Tiekink, Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 47500Bandar Sunway, Selangor Darul Ehsan, Malaysia, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Sunway University Sdn Bhd is thanked for financial support of this work through Grant No. GRTIN-IRG-01-2021.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2021-2024).

Received: 2021-04-15
Accepted: 2021-05-25
Published Online: 2021-06-14
Published in Print: 2021-06-25

© 2021 Walter de Gruyter GmbH, Berlin/Boston

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https://doi.org/10.1515/zkri-2021-2024
Keywords for this article
carbamate; computational chemistry; crystal structure analysis; dicyandiamide; Hirshfeld analysis; hydrogen bonding

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Inorganic Crystal Structures (Original Papers)
  4. ErNi2.23Al2.77 and YbNi2.31Al2.69 – i3 superstructures of the CaCu5 type
  5. New compound Sm2Ru3Sn5 with a structure derived from Ru3Sn7
  6. Site preference and atomic ordering in the ternary Rh5Ga2As: first-principles calculations
  7. SmPt2In2 – a new ternary indide with a Pt–In polyanionic framework
  8. The order/disorder phase transition of hypophosphorous acid H3PO2
  9. KCu(SeO4)Cl(H2O)2, a first copper chloride selenate
  10. The germanides APtGe2 (A = Ca, Sr, Eu)
  11. Organic and Metalorganic Crystal Structures (Original Paper)
  12. Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate
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