Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)- 2,3-dihydro-1,3,4-oxadiazole-2-thione
The title 1,3,4-oxadiazole-2-thione derivative, C18H20N4OS2, crystallized with two independent molecules (A and B) in the asymmetric unit. The 2-thienyl rings in both molecules are rotationally disordered over two orientations by approximately 180� about the single C—C bond that connects it to t...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2015
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| Online Access: | http://eprints.usm.my/38583/ http://eprints.usm.my/38583/1/Crystal_structure_of_3-%5B%284-benzylpiperazin-1-yl%29methyl%5D-5-%28thiophen-2-yl%29-.pdf |
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| author | Al-Omary, Fatmah A. M. El-Emam, Ali A. Ghabbour, Hazem A. C. S., Chidan Kumar Ching, Kheng Quah Fun, Hoong Kun |
| author_facet | Al-Omary, Fatmah A. M. El-Emam, Ali A. Ghabbour, Hazem A. C. S., Chidan Kumar Ching, Kheng Quah Fun, Hoong Kun |
| author_sort | Al-Omary, Fatmah A. M. |
| building | USM Institutional Repository |
| collection | Online Access |
| description | The title 1,3,4-oxadiazole-2-thione derivative, C18H20N4OS2,
crystallized with two independent molecules (A and B) in the
asymmetric unit. The 2-thienyl rings in both molecules are
rotationally disordered over two orientations by approximately
180� about the single C—C bond that connects it to the
oxadiazole thione ring; the ratios of site occupancies for the
major and minor components were fixed in the structure
refinement at 0.8:0.2 and 0.9:0.1 in molecules A and B,
respectively. The 1,3,4-oxadiazole-2-thione ring forms dihedral
angles of 7.71 (16), 10.0 (11) and 77.50 (12)� (molecule
A), and 6.5 (3), 6.0 (9) and 55.30 (12)� (molecule B) with the
major and minor parts of the disordered thiophene ring and
the mean plane of the adjacent piperazine ring, respectively,
resulting in approximately V-shaped conformations for the
molecules. The piperazine ring in both molecules adopts a
chair conformation. The terminal benzene ring is inclined
towards the mean plane of the piperazine ring with N—C—
C—C torsion angles of �58.2 (3) and �66.2 (3)� in molecules
A and B, respectively. In the crystal, no intermolecular
hydrogen bonds are observed. The crystal packing features
short S� � �S contacts [3.4792 (9) A ° ] and �–� interactions
[3.661 (3), 3.664 (11) and 3.5727 (10) A ° ], producing a threedimensional
network. |
| first_indexed | 2025-11-15T17:32:29Z |
| format | Article |
| id | usm-38583 |
| institution | Universiti Sains Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T17:32:29Z |
| publishDate | 2015 |
| publisher | International Union of Crystallography |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | usm-385832018-01-26T08:24:11Z http://eprints.usm.my/38583/ Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)- 2,3-dihydro-1,3,4-oxadiazole-2-thione Al-Omary, Fatmah A. M. El-Emam, Ali A. Ghabbour, Hazem A. C. S., Chidan Kumar Ching, Kheng Quah Fun, Hoong Kun QC1-999 Physics The title 1,3,4-oxadiazole-2-thione derivative, C18H20N4OS2, crystallized with two independent molecules (A and B) in the asymmetric unit. The 2-thienyl rings in both molecules are rotationally disordered over two orientations by approximately 180� about the single C—C bond that connects it to the oxadiazole thione ring; the ratios of site occupancies for the major and minor components were fixed in the structure refinement at 0.8:0.2 and 0.9:0.1 in molecules A and B, respectively. The 1,3,4-oxadiazole-2-thione ring forms dihedral angles of 7.71 (16), 10.0 (11) and 77.50 (12)� (molecule A), and 6.5 (3), 6.0 (9) and 55.30 (12)� (molecule B) with the major and minor parts of the disordered thiophene ring and the mean plane of the adjacent piperazine ring, respectively, resulting in approximately V-shaped conformations for the molecules. The piperazine ring in both molecules adopts a chair conformation. The terminal benzene ring is inclined towards the mean plane of the piperazine ring with N—C— C—C torsion angles of �58.2 (3) and �66.2 (3)� in molecules A and B, respectively. In the crystal, no intermolecular hydrogen bonds are observed. The crystal packing features short S� � �S contacts [3.4792 (9) A ° ] and �–� interactions [3.661 (3), 3.664 (11) and 3.5727 (10) A ° ], producing a threedimensional network. International Union of Crystallography 2015 Article PeerReviewed application/pdf en http://eprints.usm.my/38583/1/Crystal_structure_of_3-%5B%284-benzylpiperazin-1-yl%29methyl%5D-5-%28thiophen-2-yl%29-.pdf Al-Omary, Fatmah A. M. and El-Emam, Ali A. and Ghabbour, Hazem A. and C. S., Chidan Kumar and Ching, Kheng Quah and Fun, Hoong Kun (2015) Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)- 2,3-dihydro-1,3,4-oxadiazole-2-thione. Acta Crystallographica Section E: Crystallographic Communications, 71. 0175-0176. ISSN 2056-9890 https://doi.org/10.1107/S2056989015002273 |
| spellingShingle | QC1-999 Physics Al-Omary, Fatmah A. M. El-Emam, Ali A. Ghabbour, Hazem A. C. S., Chidan Kumar Ching, Kheng Quah Fun, Hoong Kun Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)- 2,3-dihydro-1,3,4-oxadiazole-2-thione |
| title | Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-
2,3-dihydro-1,3,4-oxadiazole-2-thione |
| title_full | Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-
2,3-dihydro-1,3,4-oxadiazole-2-thione |
| title_fullStr | Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-
2,3-dihydro-1,3,4-oxadiazole-2-thione |
| title_full_unstemmed | Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-
2,3-dihydro-1,3,4-oxadiazole-2-thione |
| title_short | Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-
2,3-dihydro-1,3,4-oxadiazole-2-thione |
| title_sort | crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-
2,3-dihydro-1,3,4-oxadiazole-2-thione |
| topic | QC1-999 Physics |
| url | http://eprints.usm.my/38583/ http://eprints.usm.my/38583/ http://eprints.usm.my/38583/1/Crystal_structure_of_3-%5B%284-benzylpiperazin-1-yl%29methyl%5D-5-%28thiophen-2-yl%29-.pdf |