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6-(4-Fluorophenyl)-8-phenyl-2,3-dihydro-4H-imidazo[5,1-b][1,3]thiazin-4-one: an unusual [6-5] fused-ring system

Gallagher, John F. orcid logoORCID: 0000-0003-4130-4556, Le Bas, Marie-Delphine H., Coleman, Claire M. and O'Shea, Donal F. (2007) 6-(4-Fluorophenyl)-8-phenyl-2,3-dihydro-4H-imidazo[5,1-b][1,3]thiazin-4-one: an unusual [6-5] fused-ring system. Acta Crystallographica Section C, 63 (3). pp. 160-162. ISSN 0108-2701

The title compound, C₁₈H₁₃FN₂OS, is the first structural example of a [6-5] fused ring incorporating the 2,3-dihydro-4H-imidazo[5,1-b][1,3]thiazin-4-one molecular scaffold. The six-membered 2,3-dihydro-1,3-thiazin-4-one ring adopts an envelope conformation, with the S-CH₂ C atom displaced by 0.761 (2) Å from the five-atom plane (all within 0.05 Å of the mean plane). The imidazole ring is planar. The phenyl ring is twisted from coplanarity with the imidazole ring by 23.84 (5)° and the 4-fluorophenyl ring is twisted by 53.36 (6)°, due to a close C(aryl)-H...O=C contact with the thiazin-4-one carbonyl O atom. The primary intermolecular interaction involves a CH₂ group with the F atom [C...F = 3.256 (2) Å and C-H...F = 137°].
Item Type:Article (Published)
Subjects:Physical Sciences > Chemistry
Physical Sciences > Crystallography
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Publisher:International Union of Crystallography
Official URL:http://dx.doi.org/10.1107/S0108270107002375
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-Share Alike 3.0 License. View License
ID Code:303
Deposited On:12 Mar 2008 by DORAS Administrator . Last Modified 10 Oct 2018 12:02

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