{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T18:07:06Z","timestamp":1785434826985,"version":"3.56.0"},"reference-count":24,"publisher":"International Union of Crystallography (IUCr)","issue":"5","license":[{"start":{"date-parts":[[2025,4,8]],"date-time":"2025-04-08T00:00:00Z","timestamp":1744070400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2025,4,8]],"date-time":"2025-04-08T00:00:00Z","timestamp":1744070400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"NSF MRI program","award":["MRI CHE1625732"],"award-info":[{"award-number":["MRI CHE1625732"]}]}],"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":[[2025,4,5]]},"published-print":{"date-parts":[[2025,5,1]]},"abstract":"<jats:p>\n                    Metconazole is a systemic triazole fungicide that inhibits the ergosterol biosynthesis pathway. It is widely used in agriculture to control fungal infections, including rusts, fusarium and septoria diseases. The molecular structure is a three-ring system, namely, 5-(4-chlorobenzyl)-2,2-dimethyl-1-(1\n                    <jats:italic>H<\/jats:italic>\n                    -1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol, C\n                    <jats:sub>17<\/jats:sub>\n                    H\n                    <jats:sub>22<\/jats:sub>\n                    ClN\n                    <jats:sub>3<\/jats:sub>\n                    O, consisting of a cyclopentan-1-ol with 1,2,4-triazol-1-ylmethyl,\n                    <jats:italic>gem<\/jats:italic>\n                    -dimethyl and 4-chlorobenzyl groups attached at the 1-, 2- and 5-positions of the cyclopentanol ring. It has two stereocentres (cyclopentanol positions 1 and 5) leading to four stereoisomers, with the (1\n                    <jats:italic>S<\/jats:italic>\n                    ,5\n                    <jats:italic>R<\/jats:italic>\n                    ) form being the most bioactive. Despite its agricultural significance, detailed crystallographic data remain scarce. This study reports the crystal structure and Hirshfeld surface analysis of racemic\n                    <jats:italic>cis<\/jats:italic>\n                    -metconazole [(1\n                    <jats:italic>S<\/jats:italic>\n                    ,5\n                    <jats:italic>R<\/jats:italic>\n                    )\/(1\n                    <jats:italic>R<\/jats:italic>\n                    ,5\n                    <jats:italic>S<\/jats:italic>\n                    )], determined in the monoclinic space group\n                    <jats:italic>P<\/jats:italic>\n                    2\n                    <jats:sub>1<\/jats:sub>\n                    \/\n                    <jats:italic>c<\/jats:italic>\n                    with two independent molecules in the asymmetric unit (\n                    <jats:italic>Z<\/jats:italic>\n                    \u2032\u00a0= 2). Both exhibit similar conformations, with minor differences in the cyclopentanol ring puckering and the torsion angles between the three rings. The crystal packing consists of 2\n                    <jats:sub>1<\/jats:sub>\n                    -screw-related hydrogen-bonded chains parallel to the\n                    <jats:italic>b<\/jats:italic>\n                    axis, with additional weak C\u2014H...N and C\u2014H...Cl contacts linking adjacent molecules. Hirshfeld surface analysis indicates that intermolecular interactions are dominated by contacts involving hydrogen (96.1 and 96.7% for the two molecules).\n                  <\/jats:p>","DOI":"10.1107\/s205698902500310x","type":"journal-article","created":{"date-parts":[[2025,4,7]],"date-time":"2025-04-07T12:26:26Z","timestamp":1744028786000},"page":"385-388","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":3,"title":["Crystal structure and Hirshfeld surface analysis of the fungicide metconazole"],"prefix":"10.1107","volume":"81","author":[{"given":"Thaluru M.","family":"Mohan Kumar","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chaluvarangaiah","family":"Sowbhagya","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9039-0273","authenticated-orcid":true,"given":"Hemmige S.","family":"Yathirajan","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/012bxv356","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5777-3918","authenticated-orcid":true,"given":"Sean","family":"Parkin","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/02k3smh20","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2025,4,8]]},"reference":[{"key":"vm2312_bb1","unstructured":"\u00c1lvarez, F., Arena, M., Auteri, D., Binaglia, S. B. L. M., Castoldi, A. F., Chiusolo, A., Colagiorgi, A., Colas, M., Crivellente, F., De Lentdecker, C., De Magistris, I., Egsmose, M., Fait, G., Ferilli, F., Gouliarmou, V., Halling, K., Nogareda, L. H., Ippolito, A., Istace, F., Jarrah, S., Kardassi, D., Kienzler, A., Lanzoni, A., Lava, R., Leuschner, R., Linguadoca, A., Louisse, J., Lythgo, C., Magrans, O., Mangas, I., Miron, I., Molnar, T., Padovani, L., Padricello, V., Panzarea, M., Morte, J. M. P., Rizzuto, S., Romac, A., Rortais, A., Serafimova, R., Sharp, R., Szentes, C., Terron, A., Theobald, A., Tiramani, M., Vianello, G. & Villamar-Bouza, L. (2023). EFSA J. 21, 8141."},{"key":"vm2312_bb2","unstructured":"Bruker (2023). APEX5. Bruker AXS Inc., Madison, Wisconsin, USA."},{"key":"vm2312_bb3","doi-asserted-by":"crossref","first-page":"5123","DOI":"10.1021\/acs.orglett.1c01651","volume":"23","author":"Budny","year":"2021","journal-title":"Org. 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