{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,1,13]],"date-time":"2025-01-13T11:40:14Z","timestamp":1736768414064,"version":"3.32.0"},"reference-count":48,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2016,3,22]],"date-time":"2016-03-22T00:00:00Z","timestamp":1458604800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2016,3,22]],"date-time":"2016-03-22T00:00:00Z","timestamp":1458604800000},"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 Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"published-print":{"date-parts":[[2016,4,1]]},"abstract":"<jats:p>Proton-pump inhibitors (PPI) are prodrugs used widely to treat acid-related diseases since the late 1980s. After an extensive research effort it has become clear that the fundamental interactions between metal atoms and PPIs are of paramount importance for both drug release and long-term therapeutic safety. Unfortunately, until now, very little information has been available on this topic. In this paper, we report the crystal structure analysis of a novel calcium\u2013PPI compound incorporating bridging and terminal deprotonated (<jats:italic>R<\/jats:italic>)-rabeprazole tricyclic ligands (<jats:italic>L<\/jats:italic>), namely bis[\u03bc-(<jats:italic>R<\/jats:italic>)-2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-6,7-dihydro-3<jats:italic>H<\/jats:italic>-benzofuro[5,6-<jats:italic>d<\/jats:italic>]imidazol-1-ido]bis{dimethanol[(<jats:italic>R<\/jats:italic>)-2-({[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methyl}sulfinyl)-6,7-dihydro-3<jats:italic>H<\/jats:italic>-benzofuro[5,6-<jats:italic>d<\/jats:italic>]imidazol-1-ido]calcium(II)} methanol hexasolvate, [Ca<jats:sub>2<\/jats:sub>(C<jats:sub>20<\/jats:sub>H<jats:sub>22<\/jats:sub>N<jats:sub>3<\/jats:sub>O<jats:sub>4<\/jats:sub>S)<jats:sub>4<\/jats:sub>(CH<jats:sub>3<\/jats:sub>OH)<jats:sub>4<\/jats:sub>]\u00b76CH<jats:sub>3<\/jats:sub>OH or [Ca<jats:sub>2<\/jats:sub>(<jats:italic>L<\/jats:italic>)<jats:sub>4<\/jats:sub>(CH<jats:sub>3<\/jats:sub>OH)<jats:sub>4<\/jats:sub>]\u00b76CH<jats:sub>3<\/jats:sub>OH, which crystallizes from methanol in the polar<jats:italic>C<\/jats:italic>2 space group. Using low-temperature microcrystal synchrotron radiation, we demonstrate that this compound is in the form of a beautiful `butterfly molecule', consisting of a<jats:italic>C<\/jats:italic><jats:sub>2<\/jats:sub>-symmetric dinuclear (CH<jats:sub>3<\/jats:sub>OH)<jats:sub>2<\/jats:sub><jats:italic>L<\/jats:italic>Ca<jats:sup>II<\/jats:sup>(\u03bc<jats:sub>2<\/jats:sub>-<jats:italic>L<\/jats:italic>)<jats:sub>2<\/jats:sub>Ca<jats:sup>II<\/jats:sup><jats:italic>L<\/jats:italic>(HOCH<jats:sub>3<\/jats:sub>)<jats:sub>2<\/jats:sub>framework. A large amount of disorder is found within the bridging<jats:italic>L<\/jats:italic>ligand and the conformation of the fused tetrahydrofuran ring exhibits great variety. All the sulfinyl groups remain intact and the nonbonded Ca...Ca distance is significantly longer than in other calcium dimers, indicating steric hindrance in the bridging ligands. Considerable hydrogen bonding and aromatic C\u2014H...\u03c0 interactions co-operate to stabilize the whole complex, as well as to facilitate supramolecular assembly. Additional investigations into the bond nature were made using density functional theory (DFT) methods at the B3LYP\/6-31G(d) level; geometry optimization, Mulliken atomic charges, MEP (molecular electrostatic potential), HOMO\u2013LUMO (highest occupied molecular orbital\u2013lowest unoccupied molecular orbital), TDOS (total density of states), PDOS (partial density of states), COOP (crystal orbital overlap population) and vibrational spectra were calculated\/recorded and assessed carefully.<\/jats:p>","DOI":"10.1107\/s2053229616004216","type":"journal-article","created":{"date-parts":[[2016,3,22]],"date-time":"2016-03-22T16:49:17Z","timestamp":1458665357000},"page":"326-336","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structure and bonding analysis of the first dinuclear calcium(II)\u2013proton-pump inhibitor (PPI) `butterfly molecule': a combined microcrystal synchrotron and DFT study"],"prefix":"10.1107","volume":"72","author":[{"given":"Hengjiang","family":"Cong","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2016,3,22]]},"reference":[{"key":"lf3028_bb1","doi-asserted-by":"crossref","first-page":"3971","DOI":"10.1016\/0277-5387(96)00140-4","volume":"15","author":"Arunasalam","year":"1996","journal-title":"Polyhedron"},{"key":"lf3028_bb2","doi-asserted-by":"crossref","first-page":"5215","DOI":"10.1021\/cr200060g","volume":"111","author":"Barreiro","year":"2011","journal-title":"Chem. 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