Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium
The crystal and molecular structures of the title molecular salts,C4H12NO+C7H5N2O4, (I), C6H16NO+C7H5N2O4, (II), and C4H12NO3+-C7H5N2O4, (III), are described. The common feature of these salts is thepresence of the 2-amino-4-nitrobenzoate anion, which exhibit non-chemicallysignificant variations in...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2018
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| Online Access: | http://eprints.sunway.edu.my/935/ http://eprints.sunway.edu.my/935/1/Edward%20Tiekink%20Crystal%20structuresActa%20Cryst.%20%282018%29%20E74%201735.pdf |
| _version_ | 1848801931831541760 |
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| author | Wardell, James L. Tiekink, Edward R. T. * |
| author_facet | Wardell, James L. Tiekink, Edward R. T. * |
| author_sort | Wardell, James L. |
| building | SU Institutional Repository |
| collection | Online Access |
| description | The crystal and molecular structures of the title molecular salts,C4H12NO+C7H5N2O4, (I), C6H16NO+C7H5N2O4, (II), and C4H12NO3+-C7H5N2O4, (III), are described. The common feature of these salts is thepresence of the 2-amino-4-nitrobenzoate anion, which exhibit non-chemicallysignificant variations in the conformational relationships between the carboxylate
and nitro groups, and between these and the benzene rings they are connected to. The number of ammonium-N—H H atoms in the cations increases from one to three in (I) to (III), respectively, and this variation significantly influences the supramolecular aggregation patterns in the respective crystals. Thus, a linear supramolecular chain along [100] sustained by charge-assisted tertiary-ammonium-N—HO(carboxylate), hydroxy-O—HO(carboxylate) and amino-N—HO(carboxylate) hydrogen-bonds is apparent in the crystal of
(I). Chains are connected into a three-dimensional architecture by methyl-C—HO(hydroxy) and – interactions, the latter between benzene rings [intercentroid separation = 3.5796 (10) A˚ ]. In the crystal of (II), a supramolecular
tube propagating along [901] arises as a result of charge-assisted secondaryammonium-N—HO(carboxylate) and hydroxy-O—HO(carboxylate) hydrogen-bonding. These are connected by methylene- and methyl-C— HO(nitro) and – stacking between benzene rings [inter-centroid separation = 3.5226 (10) A˚ ]. Finally, double-layers parallel to (100) sustained by
charge-assisted ammonium-N—HO(carboxylate), ammonium-N—H
O(hydroxy) and hydroxy-O—HO(carboxylate) hydrogen-bonds are
apparent in the crystal of (III). These are connected in a three-dimensional architecture by amine-N—HO(nitro) hydrogen-bonds. |
| first_indexed | 2025-11-14T21:15:18Z |
| format | Article |
| id | sunway-935 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:15:18Z |
| publishDate | 2018 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-9352020-10-07T08:58:28Z http://eprints.sunway.edu.my/935/ Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium Wardell, James L. Tiekink, Edward R. T. * QD Chemistry The crystal and molecular structures of the title molecular salts,C4H12NO+C7H5N2O4, (I), C6H16NO+C7H5N2O4, (II), and C4H12NO3+-C7H5N2O4, (III), are described. The common feature of these salts is thepresence of the 2-amino-4-nitrobenzoate anion, which exhibit non-chemicallysignificant variations in the conformational relationships between the carboxylate and nitro groups, and between these and the benzene rings they are connected to. The number of ammonium-N—H H atoms in the cations increases from one to three in (I) to (III), respectively, and this variation significantly influences the supramolecular aggregation patterns in the respective crystals. Thus, a linear supramolecular chain along [100] sustained by charge-assisted tertiary-ammonium-N—HO(carboxylate), hydroxy-O—HO(carboxylate) and amino-N—HO(carboxylate) hydrogen-bonds is apparent in the crystal of (I). Chains are connected into a three-dimensional architecture by methyl-C—HO(hydroxy) and – interactions, the latter between benzene rings [intercentroid separation = 3.5796 (10) A˚ ]. In the crystal of (II), a supramolecular tube propagating along [901] arises as a result of charge-assisted secondaryammonium-N—HO(carboxylate) and hydroxy-O—HO(carboxylate) hydrogen-bonding. These are connected by methylene- and methyl-C— HO(nitro) and – stacking between benzene rings [inter-centroid separation = 3.5226 (10) A˚ ]. Finally, double-layers parallel to (100) sustained by charge-assisted ammonium-N—HO(carboxylate), ammonium-N—H O(hydroxy) and hydroxy-O—HO(carboxylate) hydrogen-bonds are apparent in the crystal of (III). These are connected in a three-dimensional architecture by amine-N—HO(nitro) hydrogen-bonds. International Union of Crystallography 2018-11-02 Article PeerReviewed text en cc_by_4 http://eprints.sunway.edu.my/935/1/Edward%20Tiekink%20Crystal%20structuresActa%20Cryst.%20%282018%29%20E74%201735.pdf Wardell, James L. and Tiekink, Edward R. T. * (2018) Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium. Acta Crystallographica Section E Crystallographic Communications, 74 (12). pp. 1735-1740. ISSN 2056-9890 http://doi.org/10.1107/S2056989018015578 doi:10.1107/S2056989018015578 |
| spellingShingle | QD Chemistry Wardell, James L. Tiekink, Edward R. T. * Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium |
| title | Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium |
| title_full | Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium |
| title_fullStr | Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium |
| title_full_unstemmed | Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium |
| title_short | Crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium |
| title_sort | crystal structures of the 1:1 salts of 2-amino-4-nitrobenzoate with each of (2-hydroxyethyl)dimethylazanium, tert-butyl(2-hydroxyethyl)azanium and 1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/935/ http://eprints.sunway.edu.my/935/ http://eprints.sunway.edu.my/935/ http://eprints.sunway.edu.my/935/1/Edward%20Tiekink%20Crystal%20structuresActa%20Cryst.%20%282018%29%20E74%201735.pdf |