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

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 co...

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Main Authors: Bamigboye, C, Abbo, H. S., Kwong, Huey Chong, Tan, Sang Loon *, Tiekink, Edward R. T. *, Kamounah, F. S., Titinchi, S. J. J.
Format: Article
Language:English
Published: Oldenbough Verlag 2021
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Online Access:http://eprints.sunway.edu.my/1830/1/Tiekink%20Crystal%20Structure%20acc_z%20kristallogr%202021%20236%20187.pdf
http://eprints.sunway.edu.my/1830/
http://doi.org/10.1515/zkri-2021-2024
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spelling my.sunway.eprints.18302021-08-13T06:34:20Z http://eprints.sunway.edu.my/1830/ Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate Bamigboye, C Abbo, H. S. Kwong, Huey Chong Tan, Sang Loon * Tiekink, Edward R. T. * Kamounah, F. S. Titinchi, S. J. J. QD Chemistry 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 N–H 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. Oldenbough Verlag 2021 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1830/1/Tiekink%20Crystal%20Structure%20acc_z%20kristallogr%202021%20236%20187.pdf Bamigboye, C and Abbo, H. S. and Kwong, Huey Chong and Tan, Sang Loon * and Tiekink, Edward R. T. * and Kamounah, F. S. and Titinchi, S. J. J. (2021) Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate. Zeitschrift für Kristallographie - Crystalline Materials, 236 (5-7). pp. 187-199. ISSN 2194-4946 http://doi.org/10.1515/zkri-2021-2024 doi:10.1515/zkri-2021-2024
institution Sunway University
building Sunway Campus Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Sunway University
content_source Sunway Institutional Repository
url_provider http://eprints.sunway.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Bamigboye, C
Abbo, H. S.
Kwong, Huey Chong
Tan, Sang Loon *
Tiekink, Edward R. T. *
Kamounah, F. S.
Titinchi, S. J. J.
Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate
description 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 N–H 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.
format Article
author Bamigboye, C
Abbo, H. S.
Kwong, Huey Chong
Tan, Sang Loon *
Tiekink, Edward R. T. *
Kamounah, F. S.
Titinchi, S. J. J.
author_facet Bamigboye, C
Abbo, H. S.
Kwong, Huey Chong
Tan, Sang Loon *
Tiekink, Edward R. T. *
Kamounah, F. S.
Titinchi, S. J. J.
author_sort Bamigboye, C
title Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate
title_short Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate
title_full Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate
title_fullStr Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate
title_full_unstemmed Crystal structure analysis and supramolecular association in ethyl N-[amino(iminio)methyl]carbamate dichloride hemi-hydrate
title_sort crystal structure analysis and supramolecular association in ethyl n-[amino(iminio)methyl]carbamate dichloride hemi-hydrate
publisher Oldenbough Verlag
publishDate 2021
url http://eprints.sunway.edu.my/1830/1/Tiekink%20Crystal%20Structure%20acc_z%20kristallogr%202021%20236%20187.pdf
http://eprints.sunway.edu.my/1830/
http://doi.org/10.1515/zkri-2021-2024
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