Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2)
The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazo...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2018-12-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S205698901801561X |
| _version_ | 1798018367027675136 |
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| author | Kazuma Gotoh Hiroyuki Ishida |
| author_facet | Kazuma Gotoh Hiroyuki Ishida |
| author_sort | Kazuma Gotoh |
| collection | DOAJ |
| description | The structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazolidine-2,4-dione), C6H2Cl2O4·2C3H4N2O2, (II), have been determined at 180 K. In the crystals of both compounds, the base molecules are in the lactam form and no acid–base interaction involving H-atom transfer is observed. The asymmetric unit of (I) consists of two independent half-molecules of chloranilic acid, with each of the acid molecules lying about an inversion centre, and one ethyleneurea molecule. The asymmetric unit of (II) consists of one half-molecule of chloranilic acid, which lies about an inversion centre, and one hydantoin molecule. In the crystal of (I), the acid and base molecules are linked via O—H...O and N—H...O hydrogen bonds, forming an undulating sheet structure parallel to the ab plane. In (II), the base molecules form an inversion dimer via a pair of N—H...O hydrogen bonds, and the base dimers are further linked through another N—H...O hydrogen bond into a layer structure parallel to (\overline{1}01). The acid molecule and the base molecule are linked via an O—H...O hydrogen bond. |
| first_indexed | 2024-04-11T16:22:51Z |
| format | Article |
| id | doaj.art-090e8a2a3fdb452e933dda290d7a43d6 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T16:22:51Z |
| publishDate | 2018-12-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-090e8a2a3fdb452e933dda290d7a43d62022-12-22T04:14:16ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902018-12-0174121727173010.1107/S205698901801561Xlh5884Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2)Kazuma Gotoh0Hiroyuki Ishida1Department of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, JapanDepartment of Chemistry, Faculty of Science, Okayama University, Okayama 700-8530, JapanThe structures of the hydrogen-bonded 1:1 co-crystal of chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) with ethyleneurea (systematic name: imidazolidin-2-one), C6H2Cl2O4·C3H6N2O, (I), and the 1:2 co-crystal of chloranilic acid with hydantoin (systematic name: imidazolidine-2,4-dione), C6H2Cl2O4·2C3H4N2O2, (II), have been determined at 180 K. In the crystals of both compounds, the base molecules are in the lactam form and no acid–base interaction involving H-atom transfer is observed. The asymmetric unit of (I) consists of two independent half-molecules of chloranilic acid, with each of the acid molecules lying about an inversion centre, and one ethyleneurea molecule. The asymmetric unit of (II) consists of one half-molecule of chloranilic acid, which lies about an inversion centre, and one hydantoin molecule. In the crystal of (I), the acid and base molecules are linked via O—H...O and N—H...O hydrogen bonds, forming an undulating sheet structure parallel to the ab plane. In (II), the base molecules form an inversion dimer via a pair of N—H...O hydrogen bonds, and the base dimers are further linked through another N—H...O hydrogen bond into a layer structure parallel to (\overline{1}01). The acid molecule and the base molecule are linked via an O—H...O hydrogen bond.http://scripts.iucr.org/cgi-bin/paper?S205698901801561Xcrystal structurechloranilic acidethyleneureaimidazolidin-2-onehydantoinimidazolidine-2,4-dionehydrogen bond |
| spellingShingle | Kazuma Gotoh Hiroyuki Ishida Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2) Acta Crystallographica Section E: Crystallographic Communications crystal structure chloranilic acid ethyleneurea imidazolidin-2-one hydantoin imidazolidine-2,4-dione hydrogen bond |
| title | Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2) |
| title_full | Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2) |
| title_fullStr | Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2) |
| title_full_unstemmed | Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2) |
| title_short | Crystal structures of two hydrogen-bonded compounds of chloranilic acid–ethyleneurea (1/1) and chloranilic acid–hydantoin (1/2) |
| title_sort | crystal structures of two hydrogen bonded compounds of chloranilic acid ethyleneurea 1 1 and chloranilic acid hydantoin 1 2 |
| topic | crystal structure chloranilic acid ethyleneurea imidazolidin-2-one hydantoin imidazolidine-2,4-dione hydrogen bond |
| url | http://scripts.iucr.org/cgi-bin/paper?S205698901801561X |
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