Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione
In the title dithioglycoluril derivative, C19H20N4O3S2, there is a difference in the torsion angles between the thioimidazole moiety and the methoxyphenyl groups on either side of the molecule [C—N—Car—Car = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one side of the dithioglyco...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2019-09-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989019010764 |
| _version_ | 1819290767800139776 |
|---|---|
| author | Jonnie N. Asegbeloyin Kenechukwu J. Ifeanyieze Obinna C. Okpareke Ebube E. Oyeka Tatiana V. Groutso |
| author_facet | Jonnie N. Asegbeloyin Kenechukwu J. Ifeanyieze Obinna C. Okpareke Ebube E. Oyeka Tatiana V. Groutso |
| author_sort | Jonnie N. Asegbeloyin |
| collection | DOAJ |
| description | In the title dithioglycoluril derivative, C19H20N4O3S2, there is a difference in the torsion angles between the thioimidazole moiety and the methoxyphenyl groups on either side of the molecule [C—N—Car—Car = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one side of the dithioglycoluril moiety is slightly smaller compared to that on the opposite side, [110.9 (2)° cf. 112.0 (2)°], probably as a result of the steric effect of the methyl group. In the crystal, N—H...S hydrogen bonds link adjacent molecules to form chains propagating along the c-axis direction. The chains are linked by C—H...S hydrogen bonds, forming layers parallel to the bc plane. The layers are then linked by C—H...π interactions, leading to the formation of a three-dimensional supramolecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the molecular interactions in the crystal. |
| first_indexed | 2024-12-24T03:27:59Z |
| format | Article |
| id | doaj.art-ff8403e73d9344a8a798c3a757cc8d4f |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-24T03:27:59Z |
| publishDate | 2019-09-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-ff8403e73d9344a8a798c3a757cc8d4f2022-12-21T17:17:18ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902019-09-017591297130010.1107/S2056989019010764ex2021Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithioneJonnie N. Asegbeloyin0Kenechukwu J. Ifeanyieze1Obinna C. Okpareke2Ebube E. Oyeka3Tatiana V. Groutso4Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Enugu State, NigeriaDepartment of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Enugu State, NigeriaDepartment of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Enugu State, NigeriaDepartment of Pure and Industrial Chemistry, University of Nigeria, Nsukka 410001, Enugu State, NigeriaSchool of Chemical Sciences, the University of Auckland Private Bag 92019, Auckland 1142, New ZealandIn the title dithioglycoluril derivative, C19H20N4O3S2, there is a difference in the torsion angles between the thioimidazole moiety and the methoxyphenyl groups on either side of the molecule [C—N—Car—Car = 116.9 (2) and −86.1 (3)°, respectively]. The N—C—N bond angle on one side of the dithioglycoluril moiety is slightly smaller compared to that on the opposite side, [110.9 (2)° cf. 112.0 (2)°], probably as a result of the steric effect of the methyl group. In the crystal, N—H...S hydrogen bonds link adjacent molecules to form chains propagating along the c-axis direction. The chains are linked by C—H...S hydrogen bonds, forming layers parallel to the bc plane. The layers are then linked by C—H...π interactions, leading to the formation of a three-dimensional supramolecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the molecular interactions in the crystal.http://scripts.iucr.org/cgi-bin/paper?S2056989019010764crystal structurethioglycolurilimidazolecinnamoyl chlorideisothiocyanateN—H...S hydrogen bondingC—H...π interactions |
| spellingShingle | Jonnie N. Asegbeloyin Kenechukwu J. Ifeanyieze Obinna C. Okpareke Ebube E. Oyeka Tatiana V. Groutso Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione Acta Crystallographica Section E: Crystallographic Communications crystal structure thioglycoluril imidazole cinnamoyl chloride isothiocyanate N—H...S hydrogen bonding C—H...π interactions |
| title | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
| title_full | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
| title_fullStr | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
| title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
| title_short | Crystal structure and Hirshfeld surface analysis of a new dithioglycoluril: 1,4-bis(4-methoxyphenyl)-3a-methyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dithione |
| title_sort | crystal structure and hirshfeld surface analysis of a new dithioglycoluril 1 4 bis 4 methoxyphenyl 3a methyltetrahydroimidazo 4 5 d imidazole 2 5 1h 3h dithione |
| topic | crystal structure thioglycoluril imidazole cinnamoyl chloride isothiocyanate N—H...S hydrogen bonding C—H...π interactions |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989019010764 |
| work_keys_str_mv | AT jonnienasegbeloyin crystalstructureandhirshfeldsurfaceanalysisofanewdithioglycoluril14bis4methoxyphenyl3amethyltetrahydroimidazo45dimidazole251h3hdithione AT kenechukwujifeanyieze crystalstructureandhirshfeldsurfaceanalysisofanewdithioglycoluril14bis4methoxyphenyl3amethyltetrahydroimidazo45dimidazole251h3hdithione AT obinnacokpareke crystalstructureandhirshfeldsurfaceanalysisofanewdithioglycoluril14bis4methoxyphenyl3amethyltetrahydroimidazo45dimidazole251h3hdithione AT ebubeeoyeka crystalstructureandhirshfeldsurfaceanalysisofanewdithioglycoluril14bis4methoxyphenyl3amethyltetrahydroimidazo45dimidazole251h3hdithione AT tatianavgroutso crystalstructureandhirshfeldsurfaceanalysisofanewdithioglycoluril14bis4methoxyphenyl3amethyltetrahydroimidazo45dimidazole251h3hdithione |