{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T03:04:29Z","timestamp":1785207869631,"version":"3.55.0"},"reference-count":39,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2025,5,2]],"date-time":"2025-05-02T00:00:00Z","timestamp":1746144000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2025,5,2]],"date-time":"2025-05-02T00:00:00Z","timestamp":1746144000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemistryOpen"],"published-print":{"date-parts":[[2025,10]]},"abstract":"<jats:p>\n                    Picolinic acid and its derivatives are widely used as pendant arms in ligands for metal ion complexation, with possible biomedical applications, when exploited in the preparation of magnetic resonance imaging contrast agents and radioisotope labeling for\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010 and\n                    <jats:italic>\u03b2<\/jats:italic>\n                    \u2010therapy. Its structural and electronic characteristics make picolinic acid versatile and able to form stable complexes with various metal ions. The present study reports the synthesis of four picolinic acid derivatives useful for both coordination and bioconjugation, featuring a benzyl\u2010protected hydroxy group removable via palladium\u2010catalyzed hydrogenolysis. Chromatography and magnetic resonance\u00a0assessed the purity, identity, and structural features of the synthesized compounds, ensuring their suitability for the said applications. Single\u2010crystal X\u2010ray diffraction was exploited for structure solution of three of them, revealing that the introduction of specific substituents induces changes in both the molecular structure and the crystal packing, driven by a balance between\n                    <jats:italic>\u03c0<\/jats:italic>\n                    \u2010stacking and weak nonbonding contacts. Small changes in the pyridine substituents can induce conformational changes in the opposite benzyl ring orientation, spanning from a planar to a perpendicular orientation. The structural analysis, including Hirshfeld surfaces and energetic frameworks calculations, clarified intermolecular interactions contributing to a better understanding of the solid state behavior of the title compounds.\n                  <\/jats:p>","DOI":"10.1002\/open.202500197","type":"journal-article","created":{"date-parts":[[2025,5,2]],"date-time":"2025-05-02T08:48:44Z","timestamp":1746175724000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Unraveling the Crystal Structures of Picolinic Acid Derivatives: Synthesis, Packing, Interactions, and Conformational Flexibility"],"prefix":"10.1002","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0009-0001-8093-7084","authenticated-orcid":false,"given":"Sara","family":"Camorali","sequence":"first","affiliation":[{"name":"Dipartimento di Scienze e Innovazione Tecnologica Universit\u00e0 del Piemonte Orientale  Viale Teresa Michel 11 15121 Alessandria Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7027-8396","authenticated-orcid":false,"given":"Lorenzo","family":"Tei","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze e Innovazione Tecnologica Universit\u00e0 del Piemonte Orientale  Viale Teresa Michel 11 15121 Alessandria Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3276-8757","authenticated-orcid":false,"given":"Marco","family":"Milanesio","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze e Innovazione Tecnologica Universit\u00e0 del Piemonte Orientale  Viale Teresa Michel 11 15121 Alessandria Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6563-9364","authenticated-orcid":false,"given":"Mattia","family":"Lopresti","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze e Innovazione Tecnologica Universit\u00e0 del Piemonte Orientale  Viale Teresa Michel 11 15121 Alessandria Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,5,2]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.molpharmaceut.2c00071"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1080\/00958972.2010.499937"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.3390\/pharmaceutics13060906"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic061823d"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.0c03277"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781118503652"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.poly.2012.09.031"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.inorgchem.3c02340"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuro.2020.04.009"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/0022-1902(78)80212-7"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1186\/s41181-019-0072-5"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2004.06.018"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejic.201700176"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.9b00761"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00262-023-03461-z"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.0c00171"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.addr.2018.06.009"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1017\/S088571561900023X"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576722004708"},{"key":"e_1_2_8_21_1","volume-title":"Analisi di materiali policristallini mediante tecniche di diffrazione","author":"Guagliardi A.","year":"2008"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1107\/97809553602060000954"},{"key":"e_1_2_8_23_1","unstructured":"Agilent Technologies Ltd CrysAlis PRO Version 42.49 Yarnton2014."},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1107\/S2053273314026370"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0021889808042726"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576719014092"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1107\/S1600576721002910"},{"key":"e_1_2_8_28_1","unstructured":"M. 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