{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,22]],"date-time":"2026-07-22T23:38:36Z","timestamp":1784763516890,"version":"3.55.0"},"reference-count":28,"publisher":"International Union of Crystallography (IUCr)","issue":"11","license":[{"start":{"date-parts":[[2013,10,24]],"date-time":"2013-10-24T00:00:00Z","timestamp":1382572800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2013,10,24]],"date-time":"2013-10-24T00:00:00Z","timestamp":1382572800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst Sect C","Acta Crystallogr C","Acta Crystallogr Sect C","Acta Crystallogr Sect C Cryst Struct Commun"],"published-print":{"date-parts":[[2013,11,15]]},"abstract":"<jats:p>The X-ray single-crystal structure of (2<jats:italic>S<\/jats:italic>,5<jats:italic>R<\/jats:italic>,6<jats:italic>R<\/jats:italic>)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, commonly known as (+)-6-aminopenicillanic acid (C<jats:sub>8<\/jats:sub>H<jats:sub>12<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>3<\/jats:sub>S) and a precursor of a variety of semi-synthetic penicillins, has been determined from synchrotron data at 150\u2005K. The structure represents an ordered zwitterion and the crystals are nonmerohedrally twinned. The crystal structure is composed of a three-dimensional network built by three charge-assisted hydrogen bonds between the ammonium and carboxylate groups. The complementary analysis of the crystal packing by the<jats:italic>PIXEL<\/jats:italic>method brings to light the nature and ranking of the energetically most stabilizing intermolecular interaction energies. In accordance with the zwitterionic nature of the structure,<jats:italic>PIXEL<\/jats:italic>lattice energy calculations confirm the predominance of the Coulombic term (\u2212379.1\u2005kJ\u2005mol<jats:sup>\u22121<\/jats:sup>) ahead of the polarization (\u2212141.4\u2005kJ\u2005mol<jats:sup>\u22121<\/jats:sup>), dispersion (\u2212133.7\u2005kJ\u2005mol<jats:sup>\u22121<\/jats:sup>) and repulsion (266.3\u2005kJ\u2005mol<jats:sup>\u22121<\/jats:sup>) contributions.<\/jats:p>","DOI":"10.1107\/s0108270113025924","type":"journal-article","created":{"date-parts":[[2013,10,23]],"date-time":"2013-10-23T17:22:20Z","timestamp":1382548940000},"page":"1238-1242","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":10,"title":["Crystal structure and packing energy calculations of (+)-6-aminopenicillanic acid"],"prefix":"10.1107","volume":"69","author":[{"given":"Sofiane","family":"Saouane","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gernot","family":"Buth","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Francesca P. 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