Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO)
The crystal structures of three salicyaldoxime compounds, namely 2-hydroxy-4-methylbenzaldehyde oxime, C8H9NO2, 1, 2,4-dihydroxybenzaldehyde oxime, C7H7NO3, 2, and 2-hydroxy-4-methoxybenzaldehyde oxime, C8H9NO3, 3, are discussed. In each compound, the hydroxyl groups are essentially coplanar with th...
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International Union of Crystallography
2018-10-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989018013361 |
| _version_ | 1798019042323202048 |
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| author | Ligia R. Gomes Marcus V. N. de Souza Cristiane F. Da Costa James L. Wardell John Nicolson Low |
| author_facet | Ligia R. Gomes Marcus V. N. de Souza Cristiane F. Da Costa James L. Wardell John Nicolson Low |
| author_sort | Ligia R. Gomes |
| collection | DOAJ |
| description | The crystal structures of three salicyaldoxime compounds, namely 2-hydroxy-4-methylbenzaldehyde oxime, C8H9NO2, 1, 2,4-dihydroxybenzaldehyde oxime, C7H7NO3, 2, and 2-hydroxy-4-methoxybenzaldehyde oxime, C8H9NO3, 3, are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The interplanar angles between the C=N—O moieties of the oxime unit and their attached phenyl rings are 0.08 (9), 1.08 (15) and 6.65 (15)° in 1, 2 and 3, respectively. In all three molecules, the 2-hydroxy group forms an intramolecular O—H...N(oxime) hydrogen bond. In compound (1), intermolecular O—H(oxime)...O(hydroxyl) hydrogen bonds generate R22(14) dimers, related by inversion centres. In compound 2, intermolecular O—H(oxime)...O(4-hydroxy) hydrogen bonds generate C9 chains along the b-axis direction, while O—H(4-hydroxyl)...O(2-hydroxyl) interactions form zigzag C6 spiral chains along the c-axis direction, generated by a screw axis at 1, y, 1/4: the combination of the two chains provides a bimolecular sheet running parallel to the b axis, which lies between 0–1/2 c and 1/2–1 c. In compound 3, similar C9 chains, along the b-axis direction are generated by O—H(oxime)...O(4-methoxy) hydrogen bonds. Further weaker, C—H...π (in 1), π–π (in 2) and both C—H...π and π–π interactions (in 3) further cement the three-dimensional structures. Hirshfeld surface and fingerprint analyses are discussed. |
| first_indexed | 2024-04-11T16:34:17Z |
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| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T16:34:17Z |
| publishDate | 2018-10-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-ea47d770e0844389a7cd1988c638fae42022-12-22T04:13:54ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902018-10-0174101480148510.1107/S2056989018013361qm2128Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO)Ligia R. Gomes0Marcus V. N. de Souza1Cristiane F. Da Costa2James L. Wardell3John Nicolson Low4REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007, Porto, PortugalInstituto 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, BrazilDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, ScotlandThe crystal structures of three salicyaldoxime compounds, namely 2-hydroxy-4-methylbenzaldehyde oxime, C8H9NO2, 1, 2,4-dihydroxybenzaldehyde oxime, C7H7NO3, 2, and 2-hydroxy-4-methoxybenzaldehyde oxime, C8H9NO3, 3, are discussed. In each compound, the hydroxyl groups are essentially coplanar with their attached phenyl group. The interplanar angles between the C=N—O moieties of the oxime unit and their attached phenyl rings are 0.08 (9), 1.08 (15) and 6.65 (15)° in 1, 2 and 3, respectively. In all three molecules, the 2-hydroxy group forms an intramolecular O—H...N(oxime) hydrogen bond. In compound (1), intermolecular O—H(oxime)...O(hydroxyl) hydrogen bonds generate R22(14) dimers, related by inversion centres. In compound 2, intermolecular O—H(oxime)...O(4-hydroxy) hydrogen bonds generate C9 chains along the b-axis direction, while O—H(4-hydroxyl)...O(2-hydroxyl) interactions form zigzag C6 spiral chains along the c-axis direction, generated by a screw axis at 1, y, 1/4: the combination of the two chains provides a bimolecular sheet running parallel to the b axis, which lies between 0–1/2 c and 1/2–1 c. In compound 3, similar C9 chains, along the b-axis direction are generated by O—H(oxime)...O(4-methoxy) hydrogen bonds. Further weaker, C—H...π (in 1), π–π (in 2) and both C—H...π and π–π interactions (in 3) further cement the three-dimensional structures. Hirshfeld surface and fingerprint analyses are discussed.http://scripts.iucr.org/cgi-bin/paper?S2056989018013361crystal structurehydrogen bondingsalicylaldoximeHirshfeld surface analysis |
| spellingShingle | Ligia R. Gomes Marcus V. N. de Souza Cristiane F. Da Costa James L. Wardell John Nicolson Low Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO) Acta Crystallographica Section E: Crystallographic Communications crystal structure hydrogen bonding salicylaldoxime Hirshfeld surface analysis |
| title | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO) |
| title_full | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO) |
| title_fullStr | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO) |
| title_full_unstemmed | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO) |
| title_short | Different classical hydrogen-bonding patterns in three salicylaldoxime derivatives, 2-HO-4-XC6H3C=NOH (X = Me, OH and MeO) |
| title_sort | different classical hydrogen bonding patterns in three salicylaldoxime derivatives 2 ho 4 xc6h3c noh x me oh and meo |
| topic | crystal structure hydrogen bonding salicylaldoxime Hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989018013361 |
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