Crystal structure of a new monoclinic polymorph of 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone
The title compound, C9H11N3O2S, is a second monoclinic (P21/c) polymorph of the previously reported Cc form [Tan et al. (2008b). Acta Cryst. E64, o2224]. The molecule is non-planar, with the dihedral angle between the N3CS residue (r.m.s. deviation = 0.0816 Å) and the benzene ring being 21.36 (4)°....
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2015-01-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989014026498 |
| _version_ | 1798031886456455168 |
|---|---|
| author | M. A. Salam Mouayed A. Hussein Edward R. T. Tiekink |
| author_facet | M. A. Salam Mouayed A. Hussein Edward R. T. Tiekink |
| author_sort | M. A. Salam |
| collection | DOAJ |
| description | The title compound, C9H11N3O2S, is a second monoclinic (P21/c) polymorph of the previously reported Cc form [Tan et al. (2008b). Acta Cryst. E64, o2224]. The molecule is non-planar, with the dihedral angle between the N3CS residue (r.m.s. deviation = 0.0816 Å) and the benzene ring being 21.36 (4)°. The conformation about the C=N bond [1.292 (2) Å] is E, the two N-bound H atoms are anti, and the inner hydroxy O-bound and outer amide N-bound H atoms form intramolecular hydrogen bonds to the imine N atom. Crucially, the H atom of the outer hydroxy group is approximately syn to the H atom of the benzene C atom connecting the two C atoms bearing the hydroxy substituents. This arrangement enables the formation of supramolecular tubes aligned along [010] and sustained by N—H...O, O—H...S and N—H...S hydrogen bonds; the tubes pack with no specific interactions between them. While the molecular structure in the Cc form is comparable, the H atom of the outer hydroxy group is approximately anti, rather than syn. This different orientation leads to the formation a three-dimensional architecture based on N—H...O and O—H...S hydrogen bonds. |
| first_indexed | 2024-04-11T20:03:46Z |
| format | Article |
| id | doaj.art-9f0f9e1f0e024967b5b5b3bf17c99c65 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T20:03:46Z |
| publishDate | 2015-01-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-9f0f9e1f0e024967b5b5b3bf17c99c652022-12-22T04:05:26ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902015-01-01711586110.1107/S2056989014026498su5033Crystal structure of a new monoclinic polymorph of 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazoneM. A. Salam0Mouayed A. Hussein1Edward R. T. Tiekink2Bangladesh Petroleum Exploration and Production Co. Ltd (BAPEX), 4 Karwan Bazar, BAPEX Bhabon, Dhaka 1215, BangladeshDepartment of Chemistry, College of Science, University of Basrah, Basra 61004, IraqDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, MalaysiaThe title compound, C9H11N3O2S, is a second monoclinic (P21/c) polymorph of the previously reported Cc form [Tan et al. (2008b). Acta Cryst. E64, o2224]. The molecule is non-planar, with the dihedral angle between the N3CS residue (r.m.s. deviation = 0.0816 Å) and the benzene ring being 21.36 (4)°. The conformation about the C=N bond [1.292 (2) Å] is E, the two N-bound H atoms are anti, and the inner hydroxy O-bound and outer amide N-bound H atoms form intramolecular hydrogen bonds to the imine N atom. Crucially, the H atom of the outer hydroxy group is approximately syn to the H atom of the benzene C atom connecting the two C atoms bearing the hydroxy substituents. This arrangement enables the formation of supramolecular tubes aligned along [010] and sustained by N—H...O, O—H...S and N—H...S hydrogen bonds; the tubes pack with no specific interactions between them. While the molecular structure in the Cc form is comparable, the H atom of the outer hydroxy group is approximately anti, rather than syn. This different orientation leads to the formation a three-dimensional architecture based on N—H...O and O—H...S hydrogen bonds.http://scripts.iucr.org/cgi-bin/paper?S2056989014026498crystal structurethiosemicarbazonepolymorphconformationhydrogen bonding |
| spellingShingle | M. A. Salam Mouayed A. Hussein Edward R. T. Tiekink Crystal structure of a new monoclinic polymorph of 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone Acta Crystallographica Section E: Crystallographic Communications crystal structure thiosemicarbazone polymorph conformation hydrogen bonding |
| title | Crystal structure of a new monoclinic polymorph of 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone |
| title_full | Crystal structure of a new monoclinic polymorph of 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone |
| title_fullStr | Crystal structure of a new monoclinic polymorph of 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone |
| title_full_unstemmed | Crystal structure of a new monoclinic polymorph of 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone |
| title_short | Crystal structure of a new monoclinic polymorph of 2,4-dihydroxybenzaldehyde 4-methylthiosemicarbazone |
| title_sort | crystal structure of a new monoclinic polymorph of 2 4 dihydroxybenzaldehyde 4 methylthiosemicarbazone |
| topic | crystal structure thiosemicarbazone polymorph conformation hydrogen bonding |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989014026498 |
| work_keys_str_mv | AT masalam crystalstructureofanewmonoclinicpolymorphof24dihydroxybenzaldehyde4methylthiosemicarbazone AT mouayedahussein crystalstructureofanewmonoclinicpolymorphof24dihydroxybenzaldehyde4methylthiosemicarbazone AT edwardrttiekink crystalstructureofanewmonoclinicpolymorphof24dihydroxybenzaldehyde4methylthiosemicarbazone |