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For all four structures, the configuration across the central (formal) C=N(CN) double bond of the carbamimidothioate group is <jats:italic>Z<\/jats:italic>. The torsion angles C5\u2014O1\u2014C1\u2014S (standard sugar numbering) are all close to 180\u00b0, confirming the \u03b2 position of the substituent. Compound <jats:bold>5b<\/jats:bold> involves an intramolecular hydrogen bond N\u2014H...O1; in <jats:bold>5c<\/jats:bold> this contact is the weaker branch of a three-centre interaction, whereas in <jats:bold>5a<\/jats:bold> and <jats:bold>5d<\/jats:bold> the H...O distances are much longer and do not represent significant interactions. The C\u2014N bond lengths at the central carbon atom of the carbamimidothioate group are almost equal. All C\u2014O\u2014C=O torsion angles of the acetyl groups correspond to a synperiplanar geometry, but otherwise all four molecules display a high degree of conformational flexibility, with many widely differing torsion angles for equivalent groups. In the crystal packing, <jats:bold>5a<\/jats:bold>, <jats:bold>5c<\/jats:bold> and <jats:bold>5d<\/jats:bold> form layer structures involving the classical hydrogen bond N\u2014H...N<jats:sub>cyano<\/jats:sub> and a variety of \u2018weak\u2019 hydrogen bonds C\u2014H...O or C\u2014H...S. The packing of <jats:bold>5b<\/jats:bold> is almost featureless and involves a large number of borderline \u2018weak\u2019 hydrogen bonds. In an appendix, a potted history of wavelength preferences for structure determination is presented and it is recommended that, even for small organic crystals in non-centrosymmetric space groups, the use of Mo radiation should be considered.<\/jats:p>","DOI":"10.1107\/s2056989024006455","type":"journal-article","created":{"date-parts":[[2024,7,9]],"date-time":"2024-07-09T08:29:04Z","timestamp":1720513744000},"page":"829-839","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":6,"title":["Crystal structures of four thioglycosides involving carbamimidothioate groups"],"prefix":"10.1107","volume":"80","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7627-2286","authenticated-orcid":true,"given":"Mamdouh A.","family":"Abu-Zaied","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Galal A.","family":"Nawwar","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Galal H.","family":"Elgemeie","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter G.","family":"Jones","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2024,7,9]]},"reference":[{"key":"yz2056_bb1","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1107\/S2056989024003086","volume":"80","author":"Abu-Zaied","year":"2024","journal-title":"Acta Cryst. 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