Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents
Crystal structures are reported for three amides containing N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H...O and C—H...N hydrogen...
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| Language: | English |
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International Union of Crystallography
2021-05-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989021003637 |
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| author | Ninganayaka Mahesha Hemmige S. Yathirajan Holalagudu A. Nagma Banu Balakrishna Kalluraya Sabine Foro Christopher Glidewell |
| author_facet | Ninganayaka Mahesha Hemmige S. Yathirajan Holalagudu A. Nagma Banu Balakrishna Kalluraya Sabine Foro Christopher Glidewell |
| author_sort | Ninganayaka Mahesha |
| collection | DOAJ |
| description | Crystal structures are reported for three amides containing N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H...O and C—H...N hydrogen bonds to form ribbons of R33(19) rings, which are linked into sheets by short Br...Br interactions [3.5812 (6) Å]. N-(6-Methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide, C15H11N3O4S, crystallizes with Z′ = 2 in space group Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent molecules and a combination of two N—H...N and five C—H...O hydrogen bonds links the molecules into a three-dimensional network. The molecules of 5-cyclopropyl-N-(6-methoxybenzo[d]thiazol-2-yl)isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the methoxy group and in the cyclopropylisoxazole unit; symmetry-related pairs of molecules are linked into dimers by pairwise N—H...N hydrogen bonds. Comparisons are made with the structures of some related compounds. |
| first_indexed | 2024-12-24T00:30:42Z |
| format | Article |
| id | doaj.art-b1c0f38162ff41ff8fee4f60666bcb63 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T00:30:42Z |
| publishDate | 2021-05-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-b1c0f38162ff41ff8fee4f60666bcb632022-12-21T17:24:16ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902021-05-0177550451110.1107/S2056989021003637hb7974Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituentsNinganayaka Mahesha0Hemmige S. Yathirajan1Holalagudu A. Nagma Banu2Balakrishna Kalluraya3Sabine Foro4Christopher Glidewell5Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574199, IndiaDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore-574199, IndiaInstitute of Materials Science, Darmstadt University of Technology, Alarich-Weiss-Strasse 2, D-64287 Darmstadt, GermanySchool of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, UKCrystal structures are reported for three amides containing N-benzo[d]thiazole substituents. In N-(benzo[d]thiazol-6-yl)-3-bromobenzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the molecules are linked by N—H...O and C—H...N hydrogen bonds to form ribbons of R33(19) rings, which are linked into sheets by short Br...Br interactions [3.5812 (6) Å]. N-(6-Methoxybenzo[d]thiazol-2-yl)-2-nitrobenzamide, C15H11N3O4S, crystallizes with Z′ = 2 in space group Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent molecules and a combination of two N—H...N and five C—H...O hydrogen bonds links the molecules into a three-dimensional network. The molecules of 5-cyclopropyl-N-(6-methoxybenzo[d]thiazol-2-yl)isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the methoxy group and in the cyclopropylisoxazole unit; symmetry-related pairs of molecules are linked into dimers by pairwise N—H...N hydrogen bonds. Comparisons are made with the structures of some related compounds.http://scripts.iucr.org/cgi-bin/paper?S2056989021003637heterocyclic compoundsbenzo[d]thiazolescrystal structuremolecular conformationdisorderhydrogen bondinghalogen bonding |
| spellingShingle | Ninganayaka Mahesha Hemmige S. Yathirajan Holalagudu A. Nagma Banu Balakrishna Kalluraya Sabine Foro Christopher Glidewell Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents Acta Crystallographica Section E: Crystallographic Communications heterocyclic compounds benzo[d]thiazoles crystal structure molecular conformation disorder hydrogen bonding halogen bonding |
| title | Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents |
| title_full | Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents |
| title_fullStr | Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents |
| title_full_unstemmed | Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents |
| title_short | Different patterns of supramolecular aggregation in three amides containing N-(benzo[d]thiazolyl) substituents |
| title_sort | different patterns of supramolecular aggregation in three amides containing n benzo d thiazolyl substituents |
| topic | heterocyclic compounds benzo[d]thiazoles crystal structure molecular conformation disorder hydrogen bonding halogen bonding |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989021003637 |
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