Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation product
The syntheses and structures of an unexpected by-product from an iodination reaction, namely, ethyl 5-methyl-3-(10-nitroanthracen-9-yl)isoxazole-4-carboxylate, C21H16N2O5, (I), and its oxidation product, ethyl 3-(9-hydroxy-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate, C21H17NO5...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2022-07-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989022005710 |
| _version_ | 1811325476826775552 |
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| author | Chun Li Matthew J. Weaver Michael J. Campbell Nicholas R. Natale |
| author_facet | Chun Li Matthew J. Weaver Michael J. Campbell Nicholas R. Natale |
| author_sort | Chun Li |
| collection | DOAJ |
| description | The syntheses and structures of an unexpected by-product from an iodination reaction, namely, ethyl 5-methyl-3-(10-nitroanthracen-9-yl)isoxazole-4-carboxylate, C21H16N2O5, (I), and its oxidation product, ethyl 3-(9-hydroxy-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate, C21H17NO5 (V) are described. Compound (I) crystallizes with two molecules in the asymmetric unit in which the dihedral angles between the anthracene fused-ring systems and isoxazole ring mean planes are 88.67 (16) and 85.64 (16)°; both molecules feature a disordered nitro group. In (V), which crystallizes with one molecule in the asymmetric unit, the equivalent dihedral angle between the almost planar anthrone ring system (r.m.s. deviation = 0.029 Å) and the pendant isoxazole ring is 89.65 (5)°. In the crystal of (I), the molecules are linked by weak C—H...O interactions into a three-dimensional network and in the extended structure of (V), inversion dimers linked by pairwise O—H...O hydrogen bonds generate R22(14) loops. |
| first_indexed | 2024-04-13T14:34:56Z |
| format | Article |
| id | doaj.art-7bca91f4469d48b5bedf400ad5ac99c9 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-13T14:34:56Z |
| publishDate | 2022-07-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-7bca91f4469d48b5bedf400ad5ac99c92022-12-22T02:43:05ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902022-07-0178770370810.1107/S2056989022005710hb8020Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation productChun Li0Matthew J. Weaver1Michael J. Campbell2Nicholas R. Natale3Department of Chemistry, Ithaca College, 953 Danby Road, Ithaca, NY 14850, USADepartment of Biomedical and Pharmaceutical Sciences, University of Montana, Missoula, MT 59812, USADepartment of Biomedical and Pharmaceutical Sciences, University of Montana, Missoula, MT 59812, USADepartment of Biomedical and Pharmaceutical Sciences, University of Montana, Missoula, MT 59812, USAThe syntheses and structures of an unexpected by-product from an iodination reaction, namely, ethyl 5-methyl-3-(10-nitroanthracen-9-yl)isoxazole-4-carboxylate, C21H16N2O5, (I), and its oxidation product, ethyl 3-(9-hydroxy-10-oxo-9,10-dihydroanthracen-9-yl)-5-methylisoxazole-4-carboxylate, C21H17NO5 (V) are described. Compound (I) crystallizes with two molecules in the asymmetric unit in which the dihedral angles between the anthracene fused-ring systems and isoxazole ring mean planes are 88.67 (16) and 85.64 (16)°; both molecules feature a disordered nitro group. In (V), which crystallizes with one molecule in the asymmetric unit, the equivalent dihedral angle between the almost planar anthrone ring system (r.m.s. deviation = 0.029 Å) and the pendant isoxazole ring is 89.65 (5)°. In the crystal of (I), the molecules are linked by weak C—H...O interactions into a three-dimensional network and in the extended structure of (V), inversion dimers linked by pairwise O—H...O hydrogen bonds generate R22(14) loops.http://scripts.iucr.org/cgi-bin/paper?S2056989022005710crystal structureisoxazoleanthracenyl isoxazoleoxidation product |
| spellingShingle | Chun Li Matthew J. Weaver Michael J. Campbell Nicholas R. Natale Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation product Acta Crystallographica Section E: Crystallographic Communications crystal structure isoxazole anthracenyl isoxazole oxidation product |
| title | Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation product |
| title_full | Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation product |
| title_fullStr | Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation product |
| title_full_unstemmed | Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation product |
| title_short | Syntheses and crystal structures of a nitro–anthracene–isoxazole and its oxidation product |
| title_sort | syntheses and crystal structures of a nitro anthracene isoxazole and its oxidation product |
| topic | crystal structure isoxazole anthracenyl isoxazole oxidation product |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989022005710 |
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