High Z’ structures of 1,2,3,5-dithiadiazolyls and of 1,2,3,5-diselenadiazolyls containing the first structurally characterized monomeric diselenadiazolyls

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dc.contributor.authorBoeré, René T.
dc.contributor.authorHill, Nathan D. D.
dc.date.accessioned2019-04-25T18:08:09Z
dc.date.available2019-04-25T18:08:09Z
dc.date.issued2017
dc.descriptionSherpa Romeo yellow journal. Permission to archive accepted author manuscripten_US
dc.description.abstractCrystals of 4-[3-(trifluoromethyl)phenyl]-3H-1,2,3,5-dithiadiazol-3-yl grown by slow sublimation in a three-zone furnace form in P1 ̅ with Z = 12. The six independent molecules combine into two cis-oid and one twisted dimer, which arrange in a layer structure as two elegant clusters, with non-crystallographic four-fold and two-fold symmetry, respectively. Crystals of 4-(3-cyano-5-tertbutyl-phenyl)-3H-1,2,3,5-diselenadiazol-3-yl, formed from decomposition of a bis-diselenadiazolyl, grow in two forms under different sublimation conditions using the same furnace. The α form crystallizes in P1 ̅ with Z = 6 and the β in P21/c with Z = 20. The α polymorph consists of a distorted cis-oid dimer linked electrostatically to a monomer in the asymmetric unit. These cluster with a second unit to a centrosymmetric aggregate of six heterocycles. The β polymorph consists of clusters of four cis-oid dimers that link into chains along the b axis, whereas the fifth molecule links via -C≡N∙∙∙Se supramolecular synthons into an infinite chain of monomers also along the b axis but out-of-register with the dimer chain. A carefully curated compilation of all 83 distinct 1,2,3,5-dithiadiazolyl and of all 24 distinct 1,2,3,5diselenadiazolyl crystal structures reveals an extraordinarily large number of structures with Z' > 1 (72%) and also those with Z' ≥ 3 (24%), compared to the average for organic molecules over the whole collection in the Cambridge Structure Database. This high incidence is analyzed and attributed to competing intermolecular synthons.en_US
dc.description.peer-reviewYesen_US
dc.identifier.citationBoeré, R. T., & Hill, N. D. D. (2017). High Z’ structures of 1,2,3,5-dithiadiazolyls and of 1,2,3,5-diselenadiazolyls. CrystEngComm, 19, 3698-3707. https://doi.org/10.1039/C7CE00863Een_US
dc.identifier.urihttps://hdl.handle.net/10133/5341
dc.language.isoen_USen_US
dc.publisherRoyal Society of Chemistryen_US
dc.publisher.departmentDepartment of Chemistry and Biochemistryen_US
dc.publisher.facultyArts and Scienceen_US
dc.publisher.institutionUniversity of Lethbridgeen_US
dc.publisher.urlhttps://doi.org/10.1039/C7CE00863E
dc.subjectDithiadiazolylen_US
dc.subjectDiselenadiazolylen_US
dc.subjectRadical dimeren_US
dc.subjectHigh Z'en_US
dc.subjectMonomeric free radicalsen_US
dc.subjectSublimationen_US
dc.subjectCrystallographyen_US
dc.titleHigh Z’ structures of 1,2,3,5-dithiadiazolyls and of 1,2,3,5-diselenadiazolyls containing the first structurally characterized monomeric diselenadiazolylsen_US
dc.typeArticleen_US
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