{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T11:23:11Z","timestamp":1785410591058,"version":"3.56.0"},"reference-count":31,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2025,3,14]],"date-time":"2025-03-14T00:00:00Z","timestamp":1741910400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,3,14]],"date-time":"2025-03-14T00:00:00Z","timestamp":1741910400000},"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":[[2025,3,4]]},"published-print":{"date-parts":[[2025,4,1]]},"abstract":"<jats:p>\n                    Molecules of the title compounds, methyl (\n                    <jats:italic>Z<\/jats:italic>\n                    )-2-(4-bromophenyl)-2-[2-(4-methylphenyl)hydrazin-1-ylidene]acetate, C\n                    <jats:sub>16<\/jats:sub>\n                    H\n                    <jats:sub>15<\/jats:sub>\n                    BrN\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>\n                      <jats:italic>2<\/jats:italic>\n                    <\/jats:sub>\n                    , (\n                    <jats:bold>1<\/jats:bold>\n                    ), methyl (\n                    <jats:italic>Z<\/jats:italic>\n                    )-2-(4-bromophenyl)-2-[2-(3,5-dimethylphenyl)hydrazin-1-ylidene]acetate, C\n                    <jats:sub>17<\/jats:sub>\n                    H\n                    <jats:sub>17<\/jats:sub>\n                    BrN\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    , (\n                    <jats:bold>2<\/jats:bold>\n                    ), methyl (\n                    <jats:italic>Z<\/jats:italic>\n                    )-2-[2-(4-methoxyphenyl)hydrazin-1-ylidene]-2-(3-nitrophenyl)acetate, C\n                    <jats:sub>16<\/jats:sub>\n                    H\n                    <jats:sub>15<\/jats:sub>\n                    N\n                    <jats:sub>3<\/jats:sub>\n                    O\n                    <jats:sub>5<\/jats:sub>\n                    , (\n                    <jats:bold>3<\/jats:bold>\n                    ), and methyl (\n                    <jats:italic>Z<\/jats:italic>\n                    )-2-[2-(4-bromophenyl)hydrazin-1-ylidene]-2-(4-chlorophenyl)acetate, C\n                    <jats:sub>15<\/jats:sub>\n                    H\n                    <jats:sub>12<\/jats:sub>\n                    BrClN\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    , (\n                    <jats:bold>5<\/jats:bold>\n                    ), adopt a\n                    <jats:italic>Z<\/jats:italic>\n                    configuration with respect to the central C=N bond, while methyl (\n                    <jats:italic>E<\/jats:italic>\n                    )-2-(4-chlorophenyl)-2-(2-phenylhydrazin-1-ylidene)acetate, C\n                    <jats:sub>15<\/jats:sub>\n                    H\n                    <jats:sub>13<\/jats:sub>\n                    ClN\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    , (\n                    <jats:bold>4<\/jats:bold>\n                    ), adopts an\n                    <jats:italic>E<\/jats:italic>\n                    configuration. The atoms of the phenyl ring of the bromophenyl group of (\n                    <jats:bold>1<\/jats:bold>\n                    ) are disordered over two sets of sites with equal occupancies. In the crystal structure of (\n                    <jats:bold>1<\/jats:bold>\n                    ), molecules connected by C\u2014H...N hydrogen bonds are further linked by C\u2014H...\u03c0 interactions, forming ribbons parallel to [010]. In (\n                    <jats:bold>2<\/jats:bold>\n                    ), pairs of molecules are linked by C\u2014H...\u03c0 interactions parallel to [100]. In (\n                    <jats:bold>3<\/jats:bold>\n                    ), C\u2014H...O hydrogen bonds form ribbons parallel to [010], while in (\n                    <jats:bold>4<\/jats:bold>\n                    ), the molecules are bonded together by C\u2014H...N, C\u2014H...Cl, C\u2014H...O and C\u2014H...\u03c0 interactions parallel to [010]. In (\n                    <jats:bold>5<\/jats:bold>\n                    ), C\u2014H...Br, C\u2014H...O and C\u2014H...Cl interactions lead to the formation of layers parallel to (002). C\u2014H...\u03c0 interactions also occur between these planes. Hirshfeld surface analyses were performed to investigate and quantify the intermolecular interactions between the molecules of all compounds.\n                  <\/jats:p>","DOI":"10.1107\/s2056989025002051","type":"journal-article","created":{"date-parts":[[2025,3,13]],"date-time":"2025-03-13T06:32:11Z","timestamp":1741847531000},"page":"314-323","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structures and Hirshfeld surface analyses of methyl (2\n                    <i>Z<\/i>\n                    )-(4-bromophenyl)[2-(4-methylphenyl)hydrazinylidene]acetate, methyl (2\n                    <i>Z<\/i>\n                    )-(4-bromophenyl)[2-(3,5-dimethylphenyl)hydrazinylidene]acetate, methyl (2\n                    <i>Z<\/i>\n                    )-[2-(4-methoxyphenyl)hydrazinylidene](3-nitrophenyl)acetate, methyl (2\n                    <i>E<\/i>\n                    )-(4-chlorophenyl)(2-phenylhydrazinylidene)acetate and methyl (2\n                    <i>Z<\/i>\n                    )-[2-(4-bromophenyl)hydrazinylidene](4-chlorophenyl)acetate"],"prefix":"10.1107","volume":"81","author":[{"given":"Namiq Q.","family":"Shikhaliyev","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aliyar A.","family":"Babazade","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gulnar T.","family":"Atakishiyeva","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irada M.","family":"Shikhaliyeva","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abel M.","family":"Maharramov","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Victor N.","family":"Khrustalev","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02dn9h927","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zeliha","family":"Atio\u011flu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2421-0929","authenticated-orcid":true,"given":"Mehmet","family":"Akkurt","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2648-4686","authenticated-orcid":true,"given":"Ajaya","family":"Bhattarai","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2025,3,14]]},"reference":[{"key":"wm5749_bb1","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1016\/j.poly.2018.12.017","volume":"159","author":"Adonin","year":"2019","journal-title":"Polyhedron"},{"key":"wm5749_bb2","doi-asserted-by":"crossref","first-page":"964","DOI":"10.1107\/S2056989019007692","volume":"75","author":"Akhramez","year":"2019","journal-title":"Acta Cryst. E"},{"key":"wm5749_bb3","doi-asserted-by":"crossref","first-page":"2098","DOI":"10.1002\/jcc.27433","volume":"45","author":"Askerova","year":"2024","journal-title":"J. Comput. Chem."},{"key":"wm5749_bb4","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1107\/S0907444910048675","volume":"67","author":"Battye","year":"2011","journal-title":"Acta Cryst. D"},{"key":"wm5749_bb5","doi-asserted-by":"crossref","first-page":"1555","DOI":"10.1002\/anie.199515551","volume":"34","author":"Bernstein","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"wm5749_bb6","doi-asserted-by":"crossref","first-page":"677","DOI":"10.1016\/j.ccr.2009.09.035","volume":"254","author":"Bertani","year":"2010","journal-title":"Coord. Chem. Rev."},{"key":"wm5749_bb7","doi-asserted-by":"crossref","first-page":"4265","DOI":"10.1021\/acs.jmedchem.8b01610","volume":"62","author":"Das","year":"2019","journal-title":"J. Med. Chem."},{"key":"wm5749_bb8","unstructured":"Doyle, R. A. (2011). Marccd software manual. Rayonix L. L. C., Evanston, IL 60201, USA."},{"key":"wm5749_bb9","doi-asserted-by":"crossref","first-page":"72","DOI":"10.1107\/S0907444905036693","volume":"62","author":"Evans","year":"2006","journal-title":"Acta Cryst. D"},{"key":"wm5749_bb10","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1107\/S0021889812029111","volume":"45","author":"Farrugia","year":"2012","journal-title":"J. Appl. Cryst."},{"key":"wm5749_bb11","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"wm5749_bb12","doi-asserted-by":"crossref","first-page":"o1200","DOI":"10.1107\/S1600536811014383","volume":"67","author":"Jasinski","year":"2011","journal-title":"Acta Cryst. E"},{"key":"wm5749_bb13","doi-asserted-by":"crossref","first-page":"918","DOI":"10.1126\/science.1162215","volume":"321","author":"Metrangolo","year":"2008","journal-title":"Science"},{"key":"wm5749_bb14","doi-asserted-by":"crossref","first-page":"1194","DOI":"10.3390\/catal13081194","volume":"13","author":"Nenajdenko","year":"2023","journal-title":"Catalysts"},{"key":"wm5749_bb15","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1021\/acscatal.6b03196","volume":"7","author":"Nenajdenko","year":"2017","journal-title":"ACS Catal."},{"key":"wm5749_bb16","unstructured":"Rigaku OD (2021). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England."},{"key":"wm5749_bb17","doi-asserted-by":"crossref","first-page":"111405","DOI":"10.1016\/j.dyepig.2023.111405","volume":"217","author":"Safronov","year":"2023","journal-title":"Dyes Pigments"},{"key":"wm5749_bb18","doi-asserted-by":"crossref","first-page":"6085","DOI":"10.1002\/ejoc.202000941","author":"Sergeev","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"wm5749_bb19","doi-asserted-by":"crossref","first-page":"4964","DOI":"10.1002\/ejoc.202000807","author":"Sergeev","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"wm5749_bb20","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1070\/RCR4922","volume":"89","author":"Sergeev","year":"2020","journal-title":"Russ. Chem. Rev."},{"key":"wm5749_bb21","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"wm5749_bb22","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"wm5749_bb23","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1016\/j.mencom.2021.03.015","volume":"31","author":"Shikhaliyev","year":"2021","journal-title":"Mendeleev Commun."},{"key":"wm5749_bb24","doi-asserted-by":"crossref","first-page":"677","DOI":"10.1016\/j.mencom.2021.09.028","volume":"31","author":"Shikhaliyev","year":"2021","journal-title":"Mendeleev Commun."},{"key":"wm5749_bb25","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"wm5749_bb26","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1107\/S2056989019016244","volume":"76","author":"Spek","year":"2020","journal-title":"Acta Cryst. E"},{"key":"wm5749_bb27","doi-asserted-by":"crossref","first-page":"o751","DOI":"10.1107\/S1600536814011568","volume":"70","author":"Sultan","year":"2014","journal-title":"Acta Cryst. E"},{"key":"wm5749_bb28","doi-asserted-by":"crossref","first-page":"7024","DOI":"10.1021\/acs.joc.0c00263","volume":"85","author":"Tsyrenova","year":"2020","journal-title":"J. Org. Chem."},{"key":"wm5749_bb29","doi-asserted-by":"crossref","first-page":"480","DOI":"10.3390\/molecules25030480","volume":"25","author":"Tsyrenova","year":"2020","journal-title":"Molecules"},{"key":"wm5749_bb30","first-page":"5066","volume":"92","author":"Tsyrenova","year":"2023","journal-title":"Uspehi Himii"},{"key":"wm5749_bb31","doi-asserted-by":"crossref","first-page":"10257","DOI":"10.1021\/jm501100b","volume":"57","author":"Vitaku","year":"2014","journal-title":"J. Med. Chem."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2025\/04\/00\/wm5749\/wm5749.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2025\/04\/00\/wm5749\/wm5749.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,4,4]],"date-time":"2025-04-04T04:58:46Z","timestamp":1743742726000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989025002051"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3,14]]},"references-count":31,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2025,4]]}},"alternative-id":["S2056989025002051"],"URL":"https:\/\/doi.org\/10.1107\/s2056989025002051","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm5749sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57491sup7.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57492sup8.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57493sup9.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57494sup10.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57495sup11.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57491sup7.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57492sup8.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57493sup9.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57494sup10.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989025002051\/wm57495sup11.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,3,14]]},"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?wm5749","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":"7 January 2025","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"4 March 2025","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"14 March 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?wm5749"}},{"value":"\u00a9 2025 Shikhaliyev\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"}}]}}