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...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Oldenbough Verlag
2021
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| Online Access: | http://eprints.sunway.edu.my/1830/ http://eprints.sunway.edu.my/1830/1/Tiekink%20Crystal%20Structure%20acc_z%20kristallogr%202021%20236%20187.pdf |
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| 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 |
| building | SU Institutional Repository |
| collection | Online Access |
| 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. |
| first_indexed | 2025-11-14T21:18:39Z |
| format | Article |
| id | sunway-1830 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:18:39Z |
| publishDate | 2021 |
| publisher | Oldenbough Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-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 |
| 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 |
| title | 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_short | 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 |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1830/ http://eprints.sunway.edu.my/1830/ http://eprints.sunway.edu.my/1830/ http://eprints.sunway.edu.my/1830/1/Tiekink%20Crystal%20Structure%20acc_z%20kristallogr%202021%20236%20187.pdf |