{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,7]],"date-time":"2026-04-07T17:02:00Z","timestamp":1775581320919,"version":"3.50.1"},"reference-count":15,"publisher":"International Union of Crystallography (IUCr)","issue":"4","license":[{"start":{"date-parts":[[2026,3,24]],"date-time":"2026-03-24T00:00:00Z","timestamp":1774310400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,3,24]],"date-time":"2026-03-24T00:00:00Z","timestamp":1774310400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"The Ministry of Education and Science of Ukraine","award":["24DF037-04N (RN\/61-2024"],"award-info":[{"award-number":["24DF037-04N (RN\/61-2024"]}]}],"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":[[2026,3,18]]},"published-print":{"date-parts":[[2026,4,1]]},"abstract":"<jats:p>\n                    The title compound (systematic name: ethyl 1-{6-[4-(ethoxycarbonyl)-5-methylpyrazol-1-yl]pyridin-2-yl}-5-methylpyrazole-4-carboxylate), C\n                    <jats:sub>19<\/jats:sub>\n                    H\n                    <jats:sub>21<\/jats:sub>\n                    N\n                    <jats:sub>5<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    , consists of a central pyridine ring substituted by two functionalized pyrazole rings and crystallizes in the centrosymmetric space group\n                    <jats:italic>C<\/jats:italic>\n                    2\/\n                    <jats:italic>c<\/jats:italic>\n                    . The pyridine\u2013pyrazole and pyrazole\u2013pyrazole dihedral angles are 30.55\u2005(5) and 50.81\u2005(8)\u00b0, respectively, indicating significant deviations from coplanarity. An intramolecular C\u2014H...O hydrogen bond stabilizes the molecular conformation. In the crystal, molecules form columns along the\n                    <jats:italic>c<\/jats:italic>\n                    -axis, but large centroid separations and offsets between parallel pyridine rings contribute to the absence of \u03c0\u2013\u03c0 stacking. Intermolecular C\u2014H...N and C\u2014H...O hydrogen bonds link molecules into a three-dimensional network. Hirshfeld surface analysis shows that H...H contacts dominate the packing (49.9%), with hydrogen-involving interactions contributing over 90% of all contacts. The molecular shape is moderately anisotropic, with globularity and asphericity values of 0.677 and 0.395, respectively. These results highlight the key role of hydrogen-based interactions in directing the supramolecular organization and crystal cohesion.\n                  <\/jats:p>","DOI":"10.1107\/s2056989026002860","type":"journal-article","created":{"date-parts":[[2026,3,23]],"date-time":"2026-03-23T07:45:42Z","timestamp":1774251942000},"page":"404-407","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structure and Hirshfeld surface analysis of 2,6-bis[4-(ethoxycarbonyl)-5-methylpyrazol-1-yl]pyridine"],"prefix":"10.1107","volume":"82","author":[{"given":"Yevhen","family":"Krokhmaliuk","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Volodymyr M.","family":"Fetyukhin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0223-0363","authenticated-orcid":true,"given":"Yuliya M.","family":"Davydenko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Oleksandr S.","family":"Vynohradov","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vadim O.","family":"Pavlenko","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7050-5472","authenticated-orcid":true,"given":"Mircea-Odin","family":"Apostu","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2026,3,24]]},"reference":[{"key":"vu2017_bb1","doi-asserted-by":"crossref","first-page":"3663","DOI":"10.1016\/j.tet.2006.01.086","volume":"62","author":"Brien","year":"2006","journal-title":"Tetrahedron"},{"key":"vu2017_bb2","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. 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