{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,7]],"date-time":"2025-02-07T05:09:02Z","timestamp":1738904942412,"version":"3.37.0"},"reference-count":23,"publisher":"International Union of Crystallography (IUCr)","issue":"2","license":[{"start":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T00:00:00Z","timestamp":1736812800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T00:00:00Z","timestamp":1736812800000},"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":[[2025,1,8]]},"published-print":{"date-parts":[[2025,2,1]]},"abstract":"<jats:p>The asymmetric units of the compounds, C<jats:sub>8<\/jats:sub>H<jats:sub>5<\/jats:sub>BrCl<jats:sub>2<\/jats:sub>O (I), and C<jats:sub>9<\/jats:sub>H<jats:sub>8<\/jats:sub>Br<jats:sub>2<\/jats:sub>O (II), contain two and one crystallographically independent molecules, respectively. In compound (I), the planar rings are oriented at a dihedral angle of 13.23\u2005(8)\u00b0. In crystals of both compounds, intermolecular C\u2014H...O hydrogen bonds link the molecules into infinite chains along the <jats:italic>b<\/jats:italic>-axis direction. In crystal of (I), there are \u03c0\u2013\u03c0 interactions between the centroids of the parallel rings with centroid-to-centroid distances of 3.5974\u2005(14), 3.6178\u2005(16) and 3.9387\u2005(16)\u2005\u00c5 while neither \u03c0\u2013\u03c0 nor C\u2014H... \u03c0(ring) interactions are present in (II). The Hirshfeld surface analyses of the crystal structures indicate that the most important contributions for the crystal packings are from H...Cl\/Cl...H (27.5%), H...O\/O...H (15.0%), H...Br\/Br...H (10.2%) and H...H (9.0%) for (I) and H...Br\/Br...H (36.1%), H...H (22.2%), H...O\/O...H (14.1%) and H...C\/C...H (13.9%) for (II). Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packings. The volumes of the crystal voids and the percentages of free spaces in the unit cells were calculated to 111.55\u2005\u00c5<jats:sup>3<\/jats:sup> and 12.27% for (I) and 63.37\u2005\u00c5 and 6.69% for (II), showing that no large cavities are present in either structure.<\/jats:p>","DOI":"10.1107\/s205698902500012x","type":"journal-article","created":{"date-parts":[[2025,1,14]],"date-time":"2025-01-14T09:23:22Z","timestamp":1736846602000},"page":"120-126","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Syntheses, crystal structures, Hirshfeld surface analyses and crystal voids of 1-(4-bromophenyl)-2,2-dichloroethan-1-one and 2,2-dibromo-1-(<i>p<\/i>-tolyl)ethan-1-one"],"prefix":"10.1107","volume":"81","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1415-8012","authenticated-orcid":true,"given":"Atash V.","family":"Gurbanov","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Firudin I.","family":"Guseinov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6791-9973","authenticated-orcid":true,"given":"Aida I.","family":"Samigullina","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8602-4382","authenticated-orcid":true,"given":"Tuncer","family":"H\u00f6kelek","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Khudayar I.","family":"Hasanov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-8587-1361","authenticated-orcid":true,"given":"Tahir A.","family":"Javadzade","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4175-5656","authenticated-orcid":true,"given":"Alebel N.","family":"Belay","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2025,1,14]]},"reference":[{"key":"nx2018_bb1","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"nx2018_bb4","doi-asserted-by":"crossref","first-page":"793","DOI":"10.3390\/81100793","volume":"8","author":"Erian","year":"2003","journal-title":"Molecules"},{"key":"nx2018_bb5","doi-asserted-by":"crossref","first-page":"1019","DOI":"10.1039\/D1DT03755B","volume":"51","author":"Gurbanov","year":"2022","journal-title":"Dalton Trans."},{"key":"nx2018_bb6","doi-asserted-by":"crossref","first-page":"674","DOI":"10.1016\/j.mencom.2020.09.041","volume":"30","author":"Guseinov","year":"2020","journal-title":"Mendeleev Commun."},{"key":"nx2018_bb7","doi-asserted-by":"crossref","first-page":"327","DOI":"10.3390\/cryst7110327","volume":"7","author":"Guseinov","year":"2017","journal-title":"Crystals"},{"key":"nx2018_bb8","doi-asserted-by":"crossref","first-page":"943","DOI":"10.1007\/s10593-006-0184-1","volume":"42","author":"Guseinov","year":"2006","journal-title":"Chem. Heterocycl. Compd."},{"key":"nx2018_bb9","doi-asserted-by":"crossref","first-page":"12869","DOI":"10.1039\/D4NJ01789G","volume":"48","author":"Guseinov","year":"2024","journal-title":"New J. Chem."},{"key":"nx2018_bb10","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1107\/S2052252515012130","volume":"2","author":"Hathwar","year":"2015","journal-title":"IUCrJ"},{"key":"nx2018_bb11","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1007\/BF00549096","volume":"44","author":"Hirshfeld","year":"1977","journal-title":"Theor. Chim. Acta"},{"key":"nx2018_bb12","unstructured":"Jayatilaka, D., Grimwood, D. J., Lee, A., Lemay, A., Russel, A. J., Taylor, C., Wolff, S. K., Cassam-Chenai, P. & Whitton, A. (2005). TONTO - A System for Computational Chemistry. Available at: http:\/\/hirshfeldsurface.net\/."},{"key":"nx2018_bb13","doi-asserted-by":"crossref","first-page":"138652","DOI":"10.1016\/j.molstruc.2024.138652","volume":"1313","author":"Khalilov","year":"2024","journal-title":"J. Mol. Struct."},{"key":"nx2018_bb14","doi-asserted-by":"crossref","first-page":"213859","DOI":"10.1016\/j.ccr.2021.213859","volume":"437","author":"Ma","year":"2021","journal-title":"Coord. Chem. Rev."},{"key":"nx2018_bb15","doi-asserted-by":"crossref","first-page":"4763","DOI":"10.1002\/ejic.201700955","author":"Mahmoudi","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"nx2018_bb16","doi-asserted-by":"crossref","first-page":"3814","DOI":"10.1039\/b704980c","author":"McKinnon","year":"2007","journal-title":"Chem. Commun."},{"key":"nx2018_bb17","doi-asserted-by":"crossref","first-page":"2305","DOI":"10.1002\/ejic.201101361","volume":"2012","author":"Mizar","year":"2012","journal-title":"Eur. J. Inorg. Chem."},{"key":"nx2018_bb18","unstructured":"Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England."},{"key":"nx2018_bb19","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"nx2018_bb20","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"nx2018_bb24","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1039\/B818330A","volume":"11","author":"Spackman","year":"2009","journal-title":"CrystEngComm"},{"key":"nx2018_bb25","first-page":"377","volume":"10","author":"Spackman","year":"2008","journal-title":"CrystEngComm"},{"key":"nx2018_bb26","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"nx2018_bb27","doi-asserted-by":"crossref","first-page":"1804","DOI":"10.1039\/C0CE00683A","volume":"13","author":"Turner","year":"2011","journal-title":"CrystEngComm"},{"key":"nx2018_bb28","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1016\/j.saa.2015.09.002","volume":"153","author":"Venkatesan","year":"2016","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2025\/02\/00\/nx2018\/nx2018.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2025\/02\/00\/nx2018\/nx2018.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,2,6]],"date-time":"2025-02-06T07:23:25Z","timestamp":1738826605000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S205698902500012X"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,1,14]]},"references-count":23,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2025,2]]}},"alternative-id":["S205698902500012X"],"URL":"https:\/\/doi.org\/10.1107\/s205698902500012x","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S205698902500012X\/nx2018sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698902500012X\/nx2018Isup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S205698902500012X\/nx2018IIsup3.hkl","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"type":"electronic","value":"2056-9890"}],"subject":[],"published":{"date-parts":[[2025,1,14]]},"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?nx2018","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":"6 January 2025","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"8 January 2025","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"14 January 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?nx2018"}},{"value":"\u00a9 2025 Gurbanov 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"}}]}}