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dc.contributor.authorShreekanth, Tharangini K.
dc.contributor.authorYathirajan, Hemmige S.
dc.contributor.authorKalluraya, Balakrishna
dc.contributor.authorForo, Sabine
dc.contributor.authorGlidewell, Christopher
dc.date.accessioned2020-10-06T14:30:06Z
dc.date.available2020-10-06T14:30:06Z
dc.date.issued2020-10
dc.identifier.citationShreekanth , T K , Yathirajan , H S , Kalluraya , B , Foro , S & Glidewell , C 2020 , ' Order versus  disorder in two isomorphous pyrazolone-substituted di­ethyl propane­dioates prepared using a three-component one-pot reaction under solvent-free conditions ' , Acta Crystallographica Section E: Crystallographic Communications , vol. 76 , no. 10 , pp. 1605-1610 . https://doi.org/10.1107/S2056989020011676en
dc.identifier.issn2056-9890
dc.identifier.otherPURE: 270575768
dc.identifier.otherPURE UUID: 5f324b78-186b-49ec-95fa-1e55d045d655
dc.identifier.otherWOS: 000577165000014
dc.identifier.otherScopus: 85092444969
dc.identifier.urihttp://hdl.handle.net/10023/20731
dc.descriptionFunding for this research was provided by: University Grants Commission, New Delhi.en
dc.description.abstractTwo new substituted propane­dioate esters have been synthesized using a three-component solvent-free thermal reaction between diethyl propane­dioate (diethyl malonate), 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde and an aryl azide, forming two new C—C bonds in a single step. The products diethyl (RS)-2-[(4-bromo­phen­yl)(5-methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)meth­yl]propane­dioate, C24H25BrN2O5 (I), and diethyl (RS)-2-[(4-chloro­phen­yl)(5-methyl-3-oxo-2-phenyl-2,3-di­hydro-1H-pyrazol-4-yl)meth­yl]propane­dioate, C24H25ClN2O5 (II), are isomorphous, with Z′ = 2 in space group P21/n. The two independent mol­ecules in compound (I) are both fully ordered, while each of the independent mol­ecules in compound (II) is disordered, but in different ways. In one mol­ecule of (II), the N-phenyl ring is disordered over two sets of atomic sites having occupancies 0.635 (10) and 0.365 (10), and in the other mol­ecule the ester function is disordered over two sets of atomic sites having occupancies 0.690 (5) and 0.310 (5). In both structures, the two independent mol­ecules adopt different conformations and, in each structure, the mol­ecules are linked into complex sheets by a combination of N—H⋯O, C—H⋯O and C—H⋯π(arene) hydrogen bonds. Comparisons are made with some related structures.
dc.language.isoeng
dc.relation.ispartofActa Crystallographica Section E: Crystallographic Communicationsen
dc.rightsCopyright © 2020 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.en
dc.subjectSynthesisen
dc.subjectPyrazolesen
dc.subjectCrystal structureen
dc.subjectDisorderen
dc.subjectMolecular conformationen
dc.subjectHydrogen bondingen
dc.subjectSupramolecular assesmblyen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleOrder versus disorder in two isomorphous pyrazolone-substituted di­ethyl propane­dioates prepared using a three-component one-pot reaction under solvent-free conditionsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1107/S2056989020011676
dc.description.statusPeer revieweden


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