{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,9,11]],"date-time":"2025-09-11T18:35:38Z","timestamp":1757615738635,"version":"3.44.0"},"reference-count":12,"publisher":"International Union of Crystallography (IUCr)","issue":"8","license":[{"start":{"date-parts":[[2025,8,15]],"date-time":"2025-08-15T00:00:00Z","timestamp":1755216000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,8,15]],"date-time":"2025-08-15T00:00:00Z","timestamp":1755216000000},"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":["IUCrData","IUCr Data","International Union Crystallogr Data","Int Union Cryst Data"],"accepted":{"date-parts":[[2025,8,13]]},"published-print":{"date-parts":[[2025,8,28]]},"abstract":"<jats:p>The asymmetric unit of the title compound, C<jats:sub>3<\/jats:sub>H<jats:sub>4<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>2<\/jats:sub>, contains two coplanar molecules (<jats:italic>A<\/jats:italic> and <jats:italic>B<\/jats:italic>) completely located on mirror planes. In the crystal, N\u2014H...O, N\u2014H...N, C\u2014H...O and C\u2014H...N hydrogen bonds link the molecules into sheets parallel to (010). There are neither significant \u03c0\u2013\u03c0 nor C\u2014H...\u03c0(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packings of molecules <jats:italic>A<\/jats:italic> and <jats:italic>B<\/jats:italic> are from H...O\/O...H (32.4% for <jats:italic>A<\/jats:italic>, 30.1% for <jats:italic>B<\/jats:italic>), H...N\/N...H (28.2%, 31.5%) and H...H (12.3%, 8.0%) interactions.<\/jats:p>","DOI":"10.1107\/s2414314625007205","type":"journal-article","created":{"date-parts":[[2025,8,13]],"date-time":"2025-08-13T15:45:39Z","timestamp":1755099939000},"update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["<i>N<\/i>-(4-Amino-1,2,5-oxadiazol-3-yl)formamide"],"prefix":"10.1107","volume":"10","author":[{"given":"Firudin I.","family":"Guseinov","sequence":"first","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":"Elena V.","family":"Shuvalova","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"}]},{"given":"Nizami A.","family":"Ekberov","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\/0000-0001-9777-2653","authenticated-orcid":true,"given":"Mohammed Hadi","family":"Al-Douh","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2025,8,15]]},"reference":[{"key":"wm4232_bb1","doi-asserted-by":"crossref","first-page":"116955","DOI":"10.1016\/j.poly.2024.116955","volume":"255","author":"Aliyeva","year":"2024","journal-title":"Polyhedron"},{"key":"wm4232_bb2","doi-asserted-by":"crossref","first-page":"1817","DOI":"10.1021\/jm2013248","volume":"55","author":"Bostr\u00f6m","year":"2012","journal-title":"J. Med. Chem."},{"key":"wm4232_bb3","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"wm4232_bb4","doi-asserted-by":"crossref","first-page":"12869","DOI":"10.1039\/D4NJ01789G","volume":"48","author":"Guseinov","year":"2024","journal-title":"New J. Chem."},{"key":"wm4232_bb5","first-page":"719","volume":"66","author":"Khalilov","year":"2021","journal-title":"Rev. Roum. Chim."},{"key":"wm4232_bb6","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1016\/j.ejmech.2016.09.058","volume":"125","author":"Khan","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"wm4232_bb7","doi-asserted-by":"crossref","first-page":"933","DOI":"10.1134\/S0965544122060147","volume":"62","author":"Mahmudov","year":"2022","journal-title":"Pet. Chem."},{"key":"wm4232_bb8","unstructured":"Rigaku OD (2023). CrysAlis PRO. Oxford Diffraction, Yarnton, England."},{"key":"wm4232_bb9","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"wm4232_bb10","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"},{"key":"wm4232_bb11","doi-asserted-by":"crossref","first-page":"1006","DOI":"10.1107\/S1600576721002910","volume":"54","author":"Spackman","year":"2021","journal-title":"J. Appl. Cryst."},{"key":"wm4232_bb12","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."}],"container-title":["IUCrData"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/x\/issues\/2025\/08\/00\/wm4232\/wm4232.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/x\/issues\/2025\/08\/00\/wm4232\/wm4232.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,9,5]],"date-time":"2025-09-05T15:14:27Z","timestamp":1757085267000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2414314625007205"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,8,15]]},"references-count":12,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2025,8]]}},"alternative-id":["S2414314625007205"],"URL":"https:\/\/doi.org\/10.1107\/s2414314625007205","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2414314625007205\/wm4232sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2414314625007205\/wm4232Isup2.hkl","asserted-by":"subject"}]},"ISSN":["2414-3146"],"issn-type":[{"type":"electronic","value":"2414-3146"}],"subject":[],"published":{"date-parts":[[2025,8,15]]},"assertion":[{"value":"IUCrData","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/x"},"group":{"name":"general","label":"General"}},{"value":"data reports","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/x\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?wm4232","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":"25 June 2025","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"13 August 2025","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"15 August 2025","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This data article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?wm4232"}},{"value":"\u00a9 2025 Guseinov 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"}}],"article-number":"x250720"}}