Different molecular conformations in the crystal structures of three 5-nitroimidazolyl derivatives
The crystal structures of (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-benzyloxime, C12H12N4O3, (I), (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-fluorobenzyl) oxime, C12H11FN4O3, (II), and (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-bromobenzyl) oxime, C12H11BrN4O3, (III),...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2018-03-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989018002876 |
| _version_ | 1798031705725992960 |
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| author | Luis F. B. Osorio Samir A. Carvalho Edson F. da Silva Carlos A. M. Fraga Solange M. S. V. Wardell Bruce F. Milne James L. Wardell William T. A. Harrison |
| author_facet | Luis F. B. Osorio Samir A. Carvalho Edson F. da Silva Carlos A. M. Fraga Solange M. S. V. Wardell Bruce F. Milne James L. Wardell William T. A. Harrison |
| author_sort | Luis F. B. Osorio |
| collection | DOAJ |
| description | The crystal structures of (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-benzyloxime, C12H12N4O3, (I), (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-fluorobenzyl) oxime, C12H11FN4O3, (II), and (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-bromobenzyl) oxime, C12H11BrN4O3, (III), are described. The dihedral angle between the ring systems in (I) is 49.66 (5)° and the linking Nm—C—C=N (m = methylated) bond shows an anti conformation [torsion angle = 175.00 (15)°]. Compounds (II) and (III) are isostructural [dihedral angle between the aromatic rings = 8.31 (5)° in (II) and 5.34 (15)° in (III)] and differ from (I) in showing a near-syn conformation for the Nm—C—C=N linker [torsion angles for (II) and (III) = 17.64 (18) and 8.7 (5)°, respectively], which allows for the occurrence of a short intramolecular C—H...N contact. In the crystal of (I), C—H...N hydrogen bonds link the molecules into [010] chains, which are cross-linked by very weak C—H...O bonds into (100) sheets. Weak aromatic π–π stacking interactions occur between the sheets. The extended structures of (II) and (III) feature several C—H...N and C—H...O hydrogen bonds, which link the molecules into three-dimensional networks, which are consolidated by aromatic π–π stacking interactions. Conformational energy calculations and Hirshfeld fingerprint analyses for (I), (II) and (III) are presented and discussed. |
| first_indexed | 2024-04-11T20:00:47Z |
| format | Article |
| id | doaj.art-d17bd4b7e23641f3a2bfe478c25da1fb |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T20:00:47Z |
| publishDate | 2018-03-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-d17bd4b7e23641f3a2bfe478c25da1fb2022-12-22T04:05:38ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902018-03-0174338038410.1107/S2056989018002876mw2136Different molecular conformations in the crystal structures of three 5-nitroimidazolyl derivativesLuis F. B. Osorio0Samir A. Carvalho1Edson F. da Silva2Carlos A. M. Fraga3Solange M. S. V. Wardell4Bruce F. Milne5James L. Wardell6William T. A. Harrison7Instituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, RJ, BrazilInstituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, RJ, BrazilInstituto de Tecnologia em Fármacos e Farmanguinhos, Fundação Oswaldo Cruz, 21041-250 Rio de Janeiro, RJ, BrazilPrograma de Pesquisa em Desenvolvimento de Fármacos, Instituto de Ciências Biomédicas, Universidade Federal do Rio de Janeiro, PO Box 68023, 21941-902 Rio de Janeiro, RJ, BrazilCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, ScotlandCFisUC, Physics Department, University of Coimbra, Rua Larga 3004–516, Coimbra, PortugalDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, ScotlandDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, ScotlandThe crystal structures of (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-benzyloxime, C12H12N4O3, (I), (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-fluorobenzyl) oxime, C12H11FN4O3, (II), and (E)-1-methyl-5-nitro-1H-imidazole-2-carbaldehyde O-(4-bromobenzyl) oxime, C12H11BrN4O3, (III), are described. The dihedral angle between the ring systems in (I) is 49.66 (5)° and the linking Nm—C—C=N (m = methylated) bond shows an anti conformation [torsion angle = 175.00 (15)°]. Compounds (II) and (III) are isostructural [dihedral angle between the aromatic rings = 8.31 (5)° in (II) and 5.34 (15)° in (III)] and differ from (I) in showing a near-syn conformation for the Nm—C—C=N linker [torsion angles for (II) and (III) = 17.64 (18) and 8.7 (5)°, respectively], which allows for the occurrence of a short intramolecular C—H...N contact. In the crystal of (I), C—H...N hydrogen bonds link the molecules into [010] chains, which are cross-linked by very weak C—H...O bonds into (100) sheets. Weak aromatic π–π stacking interactions occur between the sheets. The extended structures of (II) and (III) feature several C—H...N and C—H...O hydrogen bonds, which link the molecules into three-dimensional networks, which are consolidated by aromatic π–π stacking interactions. Conformational energy calculations and Hirshfeld fingerprint analyses for (I), (II) and (III) are presented and discussed.http://scripts.iucr.org/cgi-bin/paper?S2056989018002876benzoxathiol-2-onehydrogen bondsHirshfeld surfacecrystal structure |
| spellingShingle | Luis F. B. Osorio Samir A. Carvalho Edson F. da Silva Carlos A. M. Fraga Solange M. S. V. Wardell Bruce F. Milne James L. Wardell William T. A. Harrison Different molecular conformations in the crystal structures of three 5-nitroimidazolyl derivatives Acta Crystallographica Section E: Crystallographic Communications benzoxathiol-2-one hydrogen bonds Hirshfeld surface crystal structure |
| title | Different molecular conformations in the crystal structures of three 5-nitroimidazolyl derivatives |
| title_full | Different molecular conformations in the crystal structures of three 5-nitroimidazolyl derivatives |
| title_fullStr | Different molecular conformations in the crystal structures of three 5-nitroimidazolyl derivatives |
| title_full_unstemmed | Different molecular conformations in the crystal structures of three 5-nitroimidazolyl derivatives |
| title_short | Different molecular conformations in the crystal structures of three 5-nitroimidazolyl derivatives |
| title_sort | different molecular conformations in the crystal structures of three 5 nitroimidazolyl derivatives |
| topic | benzoxathiol-2-one hydrogen bonds Hirshfeld surface crystal structure |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989018002876 |
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