{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T04:08:52Z","timestamp":1791259732030,"version":"4.1.0"},"reference-count":32,"publisher":"International Union of Crystallography (IUCr)","issue":"6","license":[{"start":{"date-parts":[[2025,5,29]],"date-time":"2025-05-29T00:00:00Z","timestamp":1748476800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},{"start":{"date-parts":[[2025,5,29]],"date-time":"2025-05-29T00:00:00Z","timestamp":1748476800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html#TDM"}],"funder":[{"name":"Vicerrector\u00eda de Investigaciones, Universidad del Quind\u00edo","award":["Project 1183"],"award-info":[{"award-number":["Project 1183"]}]},{"name":"Vicerrector\u00eda de Investigaci\u00f3n y Extensi\u00f3n, Universidad Pedag\u00f3gica y Tecnol\u00f3gica de Colombia","award":["SGI3910"],"award-info":[{"award-number":["SGI3910"]}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr C Struct Chem","Acta Crystallogr C","Acta Crystallogr C Cryst Struct Commun","Acta Cryst C","Acta Cryst C Struct Chem","Acta Cryst Sect C","Acta Cryst Sect C Struct Chem","Acta Crystallogr Sect C","Acta Crystallogr Sect C Struct Chem","Acta Crystallogr Sect C Cryst Struct Commun"],"accepted":{"date-parts":[[2025,5,13]]},"published-print":{"date-parts":[[2025,6,1]]},"abstract":"<jats:p>\n                    The pyrazole-based Schiff base (\n                    <jats:italic>E<\/jats:italic>\n                    )-3-\n                    <jats:italic>tert<\/jats:italic>\n                    -butyl-\n                    <jats:italic>N<\/jats:italic>\n                    -[(2-nitrophenyl)methylidene]-1-phenyl-1\n                    <jats:italic>H<\/jats:italic>\n                    -pyrazol-5-amine, C\n                    <jats:sub>20<\/jats:sub>\n                    H\n                    <jats:sub>20<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O\n                    <jats:sub>2<\/jats:sub>\n                    , was synthesized in a straightforward manner\n                    <jats:italic>via<\/jats:italic>\n                    a solventless maceration technique, and its structure elucidated through spectroscopic characterization and single-crystal X-ray diffraction analysis. The compound exhibits a degree of coplanarity, influenced by the\n                    <jats:italic>ortho<\/jats:italic>\n                    -nitro group on a phenyl ring. Crystal structure analysis, complemented by Hirshfeld surface analysis and QTAIM-C calculations, reveals that the crystal packing is mainly stabilized by a network of \u03c0-stacking and dispersion interactions. Notably, H...C \u03c0-stacking interactions, particularly those between\n                    <jats:italic>ortho<\/jats:italic>\n                    - and\n                    <jats:italic>para<\/jats:italic>\n                    -C\u2014H atoms of phenyl groups, play a significant role in the packing motif. The Hirshfeld surface also reveals a 5.8% contribution from H...N contacts, involving aliphatic H atoms interacting with a pyrazole N atom. CE-B3LYP calculations highlight the dominance of dispersion forces in the crystal, with the strongest interaction energy calculated to be \u221258.9\u2005kJ\u2005mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    between the central molecule and the molecular pair related by the identity symmetry operation (\n                    <jats:italic>x<\/jats:italic>\n                    ,\n                    <jats:italic>y<\/jats:italic>\n                    ,\n                    <jats:italic>z<\/jats:italic>\n                    ). These findings provide insights into the structure\u2013property relationships of this compound and contribute to understanding crystal engineering principles for designing new materials.\n                  <\/jats:p>","DOI":"10.1107\/s2053229625004334","type":"journal-article","created":{"date-parts":[[2025,5,19]],"date-time":"2025-05-19T06:17:27Z","timestamp":1747635447000},"page":"365-373","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis and crystal structure of (\n                    <i>E<\/i>\n                    )-3-\n                    <i>tert<\/i>\n                    -butyl-\n                    <i>N<\/i>\n                    -[(2-nitrophenyl)methylidene]-1-phenyl-1\n                    <i>H<\/i>\n                    -pyrazol-5-amine: a coplanar Schiff base with enhanced \u03c0-stacking interactions"],"prefix":"10.1107","volume":"81","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2997-6720","authenticated-orcid":true,"given":"Fernando","family":"Cuen\u00fa-Cabezas","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01358s213","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mayra C. Diaz","family":"Bernal","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01358s213","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jovanny A. G\u00f3mez","family":"Casta\u00f1o","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/04vdmbk59","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2025,5,29]]},"reference":[{"key":"dg3073_bb1","doi-asserted-by":"crossref","unstructured":"Bader, R. F. (1990). In Atom in Molecules: A Quantum Theory. Oxford University Press.","DOI":"10.1093\/oso\/9780198551683.001.0001"},{"key":"dg3073_bb2","doi-asserted-by":"crossref","first-page":"1489","DOI":"10.1002\/jcc.10085","volume":"23","author":"Biegler-K\u00f6nig","year":"2002","journal-title":"J. Comput. 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