{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T08:59:31Z","timestamp":1785401971341,"version":"3.56.0"},"reference-count":37,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2025,4,24]],"date-time":"2025-04-24T00:00:00Z","timestamp":1745452800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,4,24]],"date-time":"2025-04-24T00:00:00Z","timestamp":1745452800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2025,4,15]]},"published-print":{"date-parts":[[2025,5,1]]},"abstract":"<jats:p>\n                    The new phenytoin analogue 5,5-diphenyl-3-(2-propyn-1-yl)imidazolidine-2,4-dione, C\n                    <jats:sub>18<\/jats:sub>\n                    H\n                    <jats:sub>14<\/jats:sub>\n                    N\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    (\n                    <jats:bold>3<\/jats:bold>\n                    ), was obtained through an alkylation reaction with propargyl bromide\n                    <jats:italic>via<\/jats:italic>\n                    the phase-transfer catalysis method, and its structure was determined\n                    <jats:italic>via<\/jats:italic>\n                    single-crystal X-ray diffraction analysis. The asymmetric unit of\n                    <jats:bold>3<\/jats:bold>\n                    consists of two independent molecules differing mainly in the orientation of the propynyl group. Each molecule forms an inversion dimer through pairs of N2\u2014H2...O2 hydrogen bonds. The crystal structure is further consolidated by C\u2014H...O and C\u2014H...\u03c0 interactions. The contributions of the different interactions towards the crystal packing were further analysed using Hirshfeld surface and fingerprint plots, showing that the largest contribution comes from the H...H contacts (45%).\n                  <\/jats:p>","DOI":"10.1107\/s2056989025003391","type":"journal-article","created":{"date-parts":[[2025,4,17]],"date-time":"2025-04-17T01:56:46Z","timestamp":1744855006000},"page":"412-416","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-3-(prop-2-yn-1-yl)imidazolidine-2,4-dione"],"prefix":"10.1107","volume":"81","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4846-4547","authenticated-orcid":true,"given":"Abderrazzak","family":"El Moutaouakil Ala Allah","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00r8w8f84","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0230-1707","authenticated-orcid":true,"given":"Chiara","family":"Massera","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7317-4771","authenticated-orcid":true,"given":"Walid","family":"Guerrab","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00r8w8f84","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abdulsalam","family":"Alsubari","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3488-1945","authenticated-orcid":true,"given":"Joel T.","family":"Mague","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6885-5692","authenticated-orcid":true,"given":"Youssef","family":"Ramli","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/00r8w8f84","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2025,4,24]]},"reference":[{"key":"vm2311_bb1","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/j.ejmech.2018.01.021","volume":"146","author":"Aboeldahab","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"vm2311_bb2","doi-asserted-by":"crossref","unstructured":"Akrad, R., Guerrab, W., Lazrak, F., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2018c). IUCrData, 3, x180934.","DOI":"10.1107\/S2414314618000500"},{"key":"vm2311_bb3","doi-asserted-by":"crossref","first-page":"138572","DOI":"10.1016\/j.molstruc.2024.138572","volume":"1312","author":"Allah","year":"2024","journal-title":"J. Mol. Struct."},{"key":"vm2311_bb4","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1107\/S0021889804003528","volume":"37","author":"Allen","year":"2004","journal-title":"J. Appl. Cryst."},{"key":"vm2311_bb5","unstructured":"Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany."},{"key":"vm2311_bb6","unstructured":"Bruker (2016). APEX3 and SAINT. Bruker AXS, Madison, Wisconsin, USA."},{"key":"vm2311_bb7","unstructured":"El Moutaouakil Ala Allah, A., Guerrab, W., Alsubari, A., Mague, J. T. & Ramli, Y. (2023). IUCrData, 8, x230208."},{"key":"vm2311_bb8","doi-asserted-by":"crossref","first-page":"138324","DOI":"10.1016\/j.molstruc.2024.138324","volume":"1310","author":"El Moutaouakil Ala Allah","year":"2024","journal-title":"J. Mol. Struct."},{"key":"vm2311_bb9","doi-asserted-by":"crossref","first-page":"139430","DOI":"10.1016\/j.molstruc.2024.139430","volume":"1318","author":"El Moutaouakil Ala Allah","year":"2024","journal-title":"J. Mol. Struct."},{"key":"vm2311_bb10","doi-asserted-by":"crossref","first-page":"631","DOI":"10.1016\/j.jiec.2024.08.042","volume":"140","author":"Ettahiri","year":"2024","journal-title":"J. Ind. Eng. Chem."},{"key":"vm2311_bb11","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Cryst."},{"key":"vm2311_bb12","doi-asserted-by":"crossref","first-page":"6067","DOI":"10.1021\/acs.cgd.9b00863","volume":"19","author":"Giunchi","year":"2019","journal-title":"Cryst. Growth Des."},{"key":"vm2311_bb13","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"vm2311_bb14","doi-asserted-by":"crossref","first-page":"4592","DOI":"10.1080\/07391102.2022.2069865","volume":"41","author":"Guerrab","year":"2023","journal-title":"J. Biomol. Struct. Dyn."},{"key":"vm2311_bb15","doi-asserted-by":"crossref","unstructured":"Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017a). IUCrData, 2, x171534.","DOI":"10.1107\/S2414314617018089"},{"key":"vm2311_bb16","doi-asserted-by":"crossref","unstructured":"Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017b). IUCrData, 2, x171591.","DOI":"10.1107\/S2414314617018089"},{"key":"vm2311_bb17","doi-asserted-by":"crossref","unstructured":"Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017d). IUCrData, 2, x171693.","DOI":"10.1107\/S2414314617018089"},{"key":"vm2311_bb18","doi-asserted-by":"crossref","first-page":"8765","DOI":"10.1080\/07391102.2021.1922096","volume":"40","author":"Guerrab","year":"2021","journal-title":"J. Biomol. Struct. Dyn."},{"key":"vm2311_bb19","doi-asserted-by":"crossref","first-page":"8765","DOI":"10.1080\/07391102.2021.1922096","volume":"40","author":"Guerrab","year":"2022","journal-title":"J. Biomol. Struct. Dyn."},{"key":"vm2311_bb20","doi-asserted-by":"crossref","unstructured":"Guerrab, W., El Moutaouakil Ala Allah, A., Alsubari, A., Mague, J. T. & Ramli, Y. (2022b). IUCrData, 7, x220598.","DOI":"10.1107\/S2414314622005983"},{"key":"vm2311_bb21","doi-asserted-by":"crossref","unstructured":"Guerrab, W., El Moutaouakil Ala Allah, A., Alsubari, A., Mague, J. T. & Ramli, Y. (2023a). IUCrData, 8, x230060.","DOI":"10.1107\/S2414314623000603"},{"key":"vm2311_bb22","doi-asserted-by":"crossref","first-page":"127630","DOI":"10.1016\/j.molstruc.2019.127630","volume":"1205","author":"Guerrab","year":"2020","journal-title":"J. Mol. Struct."},{"key":"vm2311_bb23","doi-asserted-by":"crossref","unstructured":"Guerrab, W., Mague, J. T., Akrad, R., Ansar, M., Taoufik, J. & Ramli, Y. (2017c). IUCrData, 2, x171808.","DOI":"10.1107\/S2414314617018089"},{"key":"vm2311_bb24","doi-asserted-by":"crossref","first-page":"1425","DOI":"10.1515\/ncrs-2020-0347","volume":"235","author":"Guerrab","year":"2020","journal-title":"Z. Kristallogr. New Cryst. Struct."},{"key":"vm2311_bb25","doi-asserted-by":"crossref","unstructured":"Guerrab, W., Mague, J. T., Taoufik, J. & Ramli, Y. (2018b). IUCrData, 3, x180057.","DOI":"10.1107\/S2414314618000573"},{"key":"vm2311_bb26","doi-asserted-by":"crossref","unstructured":"Guerrab, W., Mague, J. T., Akrad, R., Ansar, M., Taoufik, J. & Ramli, Y. (2018a). IUCrData, 3, x180050.","DOI":"10.1107\/S2414314618000500"},{"key":"vm2311_bb27","doi-asserted-by":"crossref","first-page":"2290","DOI":"10.1016\/j.bmc.2012.02.009","volume":"20","author":"Handzlik","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"vm2311_bb28","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S1600576714022985","volume":"48","author":"Krause","year":"2015","journal-title":"J. Appl. Cryst."},{"key":"vm2311_bb29","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1107\/S1600576719014092","volume":"53","author":"Macrae","year":"2020","journal-title":"J. Appl. Cryst."},{"key":"vm2311_bb30","doi-asserted-by":"crossref","first-page":"2687","DOI":"10.1021\/acs.orglett.0c00642","volume":"22","author":"Neerbye Berntsen","year":"2020","journal-title":"Org. Lett."},{"key":"vm2311_bb31","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"vm2311_bb32","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"vm2311_bb33","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"vm2311_bb34","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1107\/S2056989019001129","volume":"75","author":"Tan","year":"2019","journal-title":"Acta Cryst. E"},{"key":"vm2311_bb35","doi-asserted-by":"crossref","first-page":"2163","DOI":"10.1021\/acs.cgd.8b01776","volume":"19","author":"Tri\u0161ovi\u0107","year":"2019","journal-title":"Cryst. Growth Des."},{"key":"vm2311_bb36","doi-asserted-by":"crossref","unstructured":"Vamecq, J., Van derpoorten, K., Poupaert, J. H., Balzarini, J., De Clercq, E. & Stables, J. P. (1998). Life Sci. 63, L267-P, L274.","DOI":"10.1016\/S0024-3205(98)00445-7"},{"key":"vm2311_bb37","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2025\/05\/00\/vm2311\/vm2311.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2025\/05\/00\/vm2311\/vm2311.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,6]],"date-time":"2025-05-06T11:50:57Z","timestamp":1746532257000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989025003391"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,4,24]]},"references-count":37,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2025,5]]}},"alternative-id":["S2056989025003391"],"URL":"https:\/\/doi.org\/10.1107\/s2056989025003391","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989025003391\/vm2311sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025003391\/vm2311Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025003391\/vm2311Isup3.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,4,24]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/e"},"group":{"name":"general","label":"General"}},{"value":"research communications","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?vm2311","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"17 March 2025","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"15 April 2025","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"24 April 2025","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?vm2311"}},{"value":"\u00a9 2025 El Moutaouakil Ala Allah\n                      et al.","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}},{"value":"Creative Commons Attribution (CC-BY)","order":1,"name":"license","label":"Licence","explanation":{"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}