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Single-crystal XRD revealed two crystallographically independent molecules (\n                    <jats:italic>M<\/jats:italic>\n                    1 and\n                    <jats:italic>M<\/jats:italic>\n                    2) in the asymmetric unit (\n                    <jats:italic>Z<\/jats:italic>\n                    \u2032\u00a0= 2), with small conformational differences arising mainly from the orientation variations of the peripheral substituents. In both molecules, an intramolecular O\u2014H...N(imine) hydrogen bond generates an\n                    <jats:italic>S<\/jats:italic>\n                    (6) motif that reinforces molecular planarity and \u03c0-electron delocalization. The crystal packing is dominated by heterogeneous\n                    <jats:italic>M<\/jats:italic>\n                    1...\n                    <jats:italic>M<\/jats:italic>\n                    2 contacts, whereas the homologous\n                    <jats:italic>M<\/jats:italic>\n                    1...\n                    <jats:italic>M<\/jats:italic>\n                    1 and\n                    <jats:italic>M<\/jats:italic>\n                    2...\n                    <jats:italic>M<\/jats:italic>\n                    2 interactions are comparatively less effective. C\u2014H...O and C\u2014H...N hydrogen bonds, complemented by \u03c0-related contacts, assemble the molecules into a three-dimensional supramolecular architecture. The Hirshfeld surface analysis identifies H...H, C...H\/H...C, O...H\/H...O and N...H\/H...N contacts as the principal contributors to the intermolecular organization. A Quantum Theory of Atoms in Molecules (QTAIM) analysis confirmed the intramolecular O\u2014H...N(imine) interaction through the corresponding bond critical point and associated topological descriptors and also confirmed that a secondary intramolecular C\u2014H...N(imine) contact forms a nonplanar\n                    <jats:italic>S<\/jats:italic>\n                    (6) motif. The FT\u2013IR,\n                    <jats:sup>1<\/jats:sup>\n                    H NMR and mass spectrometric data support the proposed molecular structure. The combined crystallographic, Hirshfeld surface and QTAIM analyses demonstrate the co-operative influence of hydrogen bonding and weak noncovalent interactions on the conformational stabilization and supramolecular assembly of this conjugated azo\u2013azomethine\u2013pyrazole system.\n                  <\/jats:p>","DOI":"10.1107\/s2053229626008533","type":"journal-article","created":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T07:31:07Z","timestamp":1787643067000},"page":"648-659","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Conformation and supramolecular assembly in an azo\u2013azomethine\u2013pyrazole hybrid: crystal structure, Hirshfeld surface and QTAIM analyses"],"prefix":"10.1107","volume":"82","author":[{"given":"Maria Isabel","family":"Murillo","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01358s213","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-1833-3393","authenticated-orcid":true,"given":"Yahaira","family":"Cuen\u00fa-Ibarg\u00fcen","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01358s213","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5679-2081","authenticated-orcid":true,"given":"Ronan","family":"Le Lagadec","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2997-6720","authenticated-orcid":true,"given":"Fernando","family":"Cuen\u00fa-Cabezas","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/01358s213","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6654-1315","authenticated-orcid":true,"given":"Jovanny Arles","family":"G\u00f3mez 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":[[2026,9,5]]},"reference":[{"key":"zo3074_bb1","doi-asserted-by":"crossref","unstructured":"Bader, R. 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