{"id":"https://openalex.org/W7208726423","doi":"https://doi.org/10.1107/s2053229626008533","title":"Conformation and supramolecular assembly in an azo\u2013azomethine\u2013pyrazole hybrid: crystal structure, Hirshfeld surface and QTAIM analyses","display_name":"Conformation and supramolecular assembly in an azo\u2013azomethine\u2013pyrazole hybrid: crystal structure, Hirshfeld surface and QTAIM analyses","publication_year":2026,"publication_date":"2026-08-25","ids":{"openalex":"https://openalex.org/W7208726423","doi":"https://doi.org/10.1107/s2053229626008533","pmid":"https://pubmed.ncbi.nlm.nih.gov/42695632"},"language":"en","primary_location":{"id":"doi:10.1107/s2053229626008533","doi":"https://doi.org/10.1107/s2053229626008533","is_oa":false,"landing_page_url":"https://doi.org/10.1107/s2053229626008533","pdf_url":null,"source":{"id":"https://openalex.org/S4393918092","display_name":"Acta Crystallographica Section C Structural Chemistry","issn_l":"2053-2296","issn":["2053-2296"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","medline","norway-1","poland-140","russia-white-list-2"],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Acta Crystallographica Section C Structural Chemistry","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","pubmed"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5041101114","display_name":"Mar\u00eda Isabel Murillo","orcid":"https://orcid.org/0000-0002-8729-3867","observed_orcids":["https://orcid.org/0000-0002-8729-3867"]},"institutions":[{"id":"https://openalex.org/I135437138","display_name":"Universidad del Quind\u00edo","ror":"https://ror.org/01358s213","country_code":"CO","type":"education","lineage":["https://openalex.org/I135437138"]}],"countries":["CO"],"is_corresponding":false,"raw_author_name":"Maria Isabel Murillo","raw_affiliation_strings":["Laboratorio de Qu\u00edmica Inorg\u00e1nica y Cat\u00e1lisis, Programa de Qu\u00edmica, Universidad del Quind\u00edo, Carrera 15, Calle 12 Norte, Armenia 630004, Colombia"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Laboratorio de Qu\u00edmica Inorg\u00e1nica y Cat\u00e1lisis, Programa de Qu\u00edmica, Universidad del Quind\u00edo, Carrera 15, Calle 12 Norte, Armenia 630004, Colombia","institution_ids":["https://openalex.org/I135437138"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5125527064","display_name":"YAHAIRA CUENU-IBARG\u00dcEN","orcid":"https://orcid.org/0009-0005-1833-3393","observed_orcids":["https://orcid.org/0009-0005-1833-3393"]},"institutions":[{"id":"https://openalex.org/I135437138","display_name":"Universidad del Quind\u00edo","ror":"https://ror.org/01358s213","country_code":"CO","type":"education","lineage":["https://openalex.org/I135437138"]}],"countries":["CO"],"is_corresponding":false,"raw_author_name":"Yahaira Cuen\u00fa-Ibarg\u00fcen","raw_affiliation_strings":["Laboratorio de Qu\u00edmica Inorg\u00e1nica y Cat\u00e1lisis, Programa de Qu\u00edmica, Universidad del Quind\u00edo, Carrera 15, Calle 12 Norte, Armenia 630004, Colombia"],"raw_orcid":"https://orcid.org/0009-0005-1833-3393","affiliations":[{"raw_affiliation_string":"Laboratorio de Qu\u00edmica Inorg\u00e1nica y Cat\u00e1lisis, Programa de Qu\u00edmica, Universidad del Quind\u00edo, Carrera 15, Calle 12 Norte, Armenia 630004, Colombia","institution_ids":["https://openalex.org/I135437138"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5038859761","display_name":"Ronan Le Lagadec","orcid":"https://orcid.org/0000-0002-5679-2081","observed_orcids":["https://orcid.org/0000-0002-5679-2081"]},"institutions":[{"id":"https://openalex.org/I8961855","display_name":"Universidad Nacional Aut\u00f3noma de M\u00e9xico","ror":"https://ror.org/01tmp8f25","country_code":"MX","type":"education","lineage":["https://openalex.org/I8961855"]}],"countries":["MX"],"is_corresponding":false,"raw_author_name":"Ronan Le Lagadec","raw_affiliation_strings":["Instituto de Qu\u00edmica UNAM, Circuito Exterior s/n, Ciudad Universitaria, 04510 Ciudad de M\u00e9xico, Mexico"],"raw_orcid":"https://orcid.org/0000-0002-5679-2081","affiliations":[{"raw_affiliation_string":"Instituto de Qu\u00edmica UNAM, Circuito Exterior s/n, Ciudad Universitaria, 04510 Ciudad de M\u00e9xico, Mexico","institution_ids":["https://openalex.org/I8961855"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5011711070","display_name":"Fernando Cuen\u00fa Cabezas","orcid":"https://orcid.org/0000-0003-2997-6720","observed_orcids":["https://orcid.org/0000-0003-2997-6720"]},"institutions":[{"id":"https://openalex.org/I135437138","display_name":"Universidad del Quind\u00edo","ror":"https://ror.org/01358s213","country_code":"CO","type":"education","lineage":["https://openalex.org/I135437138"]}],"countries":["CO"],"is_corresponding":false,"raw_author_name":"Fernando Cuen\u00fa-Cabezas","raw_affiliation_strings":["Laboratorio de Qu\u00edmica Inorg\u00e1nica y Cat\u00e1lisis, Programa de Qu\u00edmica, Universidad del Quind\u00edo, Carrera 15, Calle 12 Norte, Armenia 630004, Colombia"],"raw_orcid":"https://orcid.org/0000-0003-2997-6720","affiliations":[{"raw_affiliation_string":"Laboratorio de Qu\u00edmica Inorg\u00e1nica y Cat\u00e1lisis, Programa de Qu\u00edmica, Universidad del Quind\u00edo, Carrera 15, Calle 12 Norte, Armenia 630004, Colombia","institution_ids":["https://openalex.org/I135437138"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5074078700","display_name":"Jovanny A. G\u00f3mez Casta\u00f1o","orcid":"https://orcid.org/0000-0002-6654-1315","observed_orcids":["https://orcid.org/0000-0002-6654-1315"]},"institutions":[{"id":"https://openalex.org/I222202552","display_name":"Universidad Pedag\u00f3gica y Tecnol\u00f3gica de Colombia","ror":"https://ror.org/04vdmbk59","country_code":"CO","type":"education","lineage":["https://openalex.org/I222202552"]}],"countries":["CO"],"is_corresponding":false,"raw_author_name":"Jovanny Arles G\u00f3mez Casta\u00f1o","raw_affiliation_strings":["Grupo Qu\u00edmica-F\u00edsica Molecular y Modelamiento Computacional (QUIMOL), Escuela de Ciencias Qu\u00edmicas, Universidad Pedag\u00f3gica y Tecnol\u00f3gica de Colombia, Sede Central, Avenida Central del Norte, Tunja 150003, Colombia"],"raw_orcid":"https://orcid.org/0000-0002-6654-1315","affiliations":[{"raw_affiliation_string":"Grupo Qu\u00edmica-F\u00edsica Molecular y Modelamiento Computacional (QUIMOL), Escuela de Ciencias Qu\u00edmicas, Universidad Pedag\u00f3gica y Tecnol\u00f3gica de Colombia, Sede Central, Avenida Central del Norte, Tunja 150003, Colombia","institution_ids":["https://openalex.org/I222202552"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":3,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":{"value":3950,"currency":"USD","value_usd":3950},"apc_paid":null,"fwci":0.0,"has_fulltext":false,"cited_by_count":0,"citation_normalized_percentile":{"value":0.0,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":null,"biblio":{"volume":"82","issue":"10","first_page":"648","last_page":"659"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10464","display_name":"Crystal structures of chemical compounds","score":0.9330999851226807,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10464","display_name":"Crystal structures of chemical compounds","score":0.9330999851226807,"subfield":{"id":"https://openalex.org/subfields/1604","display_name":"Inorganic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10798","display_name":"Crystallography and molecular interactions","score":0.06520000100135803,"subfield":{"id":"https://openalex.org/subfields/1606","display_name":"Physical and Theoretical Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T11025","display_name":"Nonlinear Optical Materials Research","score":0.00039999998989515007,"subfield":{"id":"https://openalex.org/subfields/2504","display_name":"Electronic, Optical and Magnetic Materials"},"field":{"id":"https://openalex.org/fields/25","display_name":"Materials Science"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/donor-pi-acceptor-systems","display_name":"donor-\u03c0-acceptor systems","score":0.8349999785423279},{"id":"https://openalex.org/keywords/supramolecular-self-assembly","display_name":"supramolecular self-assembly","score":0.8519999980926514},{"id":"https://openalex.org/keywords/crystal-structure","display_name":"crystal structure","score":0.6589999794960022},{"id":"https://openalex.org/keywords/hirshfeld-surface-analysis","display_name":"Hirshfeld surface analysis","score":0.7839999794960022},{"id":"https://openalex.org/keywords/qtaim","display_name":"QTAIM","score":0.8059999942779541},{"id":"https://openalex.org/keywords/intramolecular-hydrogen-bonding","display_name":"intramolecular hydrogen bonding","score":0.8389999866485596},{"id":"https://openalex.org/keywords/o-hn-hydrogen-bonds","display_name":"O-H\u22efN hydrogen bonds","score":0.828000009059906},{"id":"https://openalex.org/keywords/s-6-ring-motif","display_name":"S(6) ring motif","score":0.6449999809265137},{"id":"https://openalex.org/keywords/crystal-packing","display_name":"crystal packing","score":0.6819999814033508},{"id":"https://openalex.org/keywords/c-hpi-interactions","display_name":"C-H\u22ef\u03c0 interactions","score":0.8169999718666077},{"id":"https://openalex.org/keywords/molecular-conformation","display_name":"molecular conformation","score":0.6940000057220459}],"concepts":[{"id":"https://openalex.org/C75079739","wikidata":"https://www.wikidata.org/wiki/Q1571801","display_name":"Intramolecular force","level":2,"score":0.848800003528595},{"id":"https://openalex.org/C93275456","wikidata":"https://www.wikidata.org/wiki/Q756449","display_name":"Supramolecular chemistry","level":3,"score":0.7813000082969666},{"id":"https://openalex.org/C8010536","wikidata":"https://www.wikidata.org/wiki/Q160398","display_name":"Crystallography","level":1,"score":0.7339000105857849},{"id":"https://openalex.org/C166950319","wikidata":"https://www.wikidata.org/wiki/Q245031","display_name":"Intermolecular force","level":3,"score":0.7247999906539917},{"id":"https://openalex.org/C112887158","wikidata":"https://www.wikidata.org/wiki/Q169324","display_name":"Hydrogen bond","level":3,"score":0.7041000127792358},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6402000188827515},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.5982999801635742},{"id":"https://openalex.org/C137277065","wikidata":"https://www.wikidata.org/wiki/Q2915446","display_name":"Non-covalent interactions","level":4,"score":0.5982999801635742},{"id":"https://openalex.org/C63385615","wikidata":"https://www.wikidata.org/wiki/Q2869600","display_name":"Atoms in molecules","level":3,"score":0.5426999926567078},{"id":"https://openalex.org/C192406513","wikidata":"https://www.wikidata.org/wiki/Q2427921","display_name":"Supramolecular assembly","level":4,"score":0.5034999847412109},{"id":"https://openalex.org/C115624301","wikidata":"https://www.wikidata.org/wiki/Q895901","display_name":"Crystal structure","level":2,"score":0.4422999918460846},{"id":"https://openalex.org/C112613896","wikidata":"https://www.wikidata.org/wiki/Q898370","display_name":"Conjugated system","level":3,"score":0.39879998564720154},{"id":"https://openalex.org/C68260962","wikidata":"https://www.wikidata.org/wiki/Q7200967","display_name":"Planarity testing","level":2,"score":0.38339999318122864},{"id":"https://openalex.org/C2781285689","wikidata":"https://www.wikidata.org/wiki/Q21921428","display_name":"Crystal (programming language)","level":2,"score":0.37130001187324524},{"id":"https://openalex.org/C66974803","wikidata":"https://www.wikidata.org/wiki/Q10359898","display_name":"Nuclear magnetic resonance spectroscopy","level":2,"score":0.3504999876022339},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.30059999227523804},{"id":"https://openalex.org/C5716244","wikidata":"https://www.wikidata.org/wiki/Q5191408","display_name":"Crystal engineering","level":4,"score":0.2838999927043915},{"id":"https://openalex.org/C130929614","wikidata":"https://www.wikidata.org/wiki/Q7644706","display_name":"Supramolecular polymers","level":4,"score":0.2556000053882599},{"id":"https://openalex.org/C179303850","wikidata":"https://www.wikidata.org/wiki/Q4300362","display_name":"Molecular recognition","level":3,"score":0.25099998712539673}],"mesh":[],"locations_count":2,"locations":[{"id":"doi:10.1107/s2053229626008533","doi":"https://doi.org/10.1107/s2053229626008533","is_oa":false,"landing_page_url":"https://doi.org/10.1107/s2053229626008533","pdf_url":null,"source":{"id":"https://openalex.org/S4393918092","display_name":"Acta Crystallographica Section C Structural Chemistry","issn_l":"2053-2296","issn":["2053-2296"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-c","jufo-1","medline","norway-1","poland-140","russia-white-list-2"],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Acta Crystallographica Section C Structural Chemistry","raw_type":"journal-article"},{"id":"pmid:42695632","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/42695632","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Acta crystallographica. Section C, Structural chemistry","raw_type":"Journal Article"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320316911","display_name":"Universidad del Quind\u00edo","ror":"https://ror.org/01358s213"},{"id":"https://openalex.org/F4320318903","display_name":"Universidad Pedag\u00f3gica y Tecnol\u00f3gica de Colombia","ror":"https://ror.org/04vdmbk59"}],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":27,"referenced_works":["https://openalex.org/W1969360633","https://openalex.org/W2088702507","https://openalex.org/W2141074519","https://openalex.org/W2319902168","https://openalex.org/W2731568958","https://openalex.org/W2751702258","https://openalex.org/W2809687979","https://openalex.org/W2912724736","https://openalex.org/W2914372734","https://openalex.org/W2949902631","https://openalex.org/W3159829212","https://openalex.org/W3195651943","https://openalex.org/W4200011744","https://openalex.org/W4200340230","https://openalex.org/W4210673469","https://openalex.org/W4285033966","https://openalex.org/W4289544240","https://openalex.org/W4388166534","https://openalex.org/W4397001826","https://openalex.org/W4403397044","https://openalex.org/W4409958923","https://openalex.org/W4410839464","https://openalex.org/W4413992063","https://openalex.org/W4415127045","https://openalex.org/W7083014470","https://openalex.org/W7138939296","https://openalex.org/W7171316672"],"related_works":["https://openalex.org/W2779634046","https://openalex.org/W7140229435","https://openalex.org/W4245106980","https://openalex.org/W4205855453","https://openalex.org/W2757332287","https://openalex.org/W7167458933","https://openalex.org/W3206872135","https://openalex.org/W4413416634","https://openalex.org/W3032997885","https://openalex.org/W4401599212"],"abstract_inverted_index":{"An":[0],"azo\u2013azomethine\u2013pyrazole":[1,240],"hybrid,":[2],"namely,":[3],"2-({[3-":[4],"tert":[5],"-butyl-1-(4-nitrophenyl)-1":[6],"H":[7,11,200],"-pyrazol-5-yl]imino}methyl)-4-[(4-methylphenyl)diazenyl]phenol,":[8],"C":[9],"27":[10],"26":[12],"N":[13],"6":[14],"O":[15],"3":[16],",":[17],"crystallizes":[18],"as":[19,150],"an":[20,32,76,82],"extended":[21],"donor\u2013\u03c0\u2013acceptor":[22],"system":[23],"that":[24,86,185],"combines":[25],"azo,":[26],"azomethine":[27],"and":[28,47,90,112,123,147,178,182,202,216,226,234],"pyrazole":[29],"fragments":[30],"within":[31],"almost":[33],"coplanar":[34],"conjugated":[35,239],"framework.":[36],"Single-crystal":[37],"XRD":[38],"revealed":[39],"two":[40],"crystallographically":[41],"independent":[42],"molecules":[43,133],"(":[44,54],"M":[45,48,100,102,108,110,113,115],"1":[46,111,199],"2)":[49],"in":[50,163],"the":[51,66,70,106,132,151,155,168,173,207,220,231],"asymmetric":[52],"unit":[53],"Z":[55],"\u2032":[56],"=":[57],"2),":[58],"with":[59],"small":[60],"conformational":[61,232],"differences":[62],"arising":[63],"mainly":[64],"from":[65],"orientation":[67],"variations":[68],"of":[69,161,223,237],"peripheral":[71],"substituents.":[72],"In":[73],"both":[74],"molecules,":[75],"intramolecular":[77,169,188],"O\u2014H...N(imine)":[78,170],"hydrogen":[79,125,224],"bond":[80,175],"generates":[81],"S":[83,194],"(6)":[84,195],"motif":[85],"reinforces":[87],"molecular":[88,209],"planarity":[89],"\u03c0-electron":[91],"delocalization.":[92],"The":[93,139,197,211],"crystal":[94],"packing":[95],"is":[96],"dominated":[97],"by":[98,128],"heterogeneous":[99],"1...":[101,109],"2":[103,116],"contacts,":[104,130],"whereas":[105],"homologous":[107],"2...":[114],"interactions":[117,229],"are":[118],"comparatively":[119],"less":[120],"effective.":[121],"C\u2014H...O":[122],"C\u2014H...N":[124],"bonds,":[126],"complemented":[127],"\u03c0-related":[129],"assemble":[131],"into":[134],"a":[135,186,192],"three-dimensional":[136],"supramolecular":[137,235],"architecture.":[138],"Hirshfeld":[140,214],"surface":[141,215],"analysis":[142,166],"identifies":[143],"H...H,":[144],"C...H/H...C,":[145],"O...H/H...O":[146],"N...H/H...N":[148],"contacts":[149],"principal":[152],"contributors":[153],"to":[154],"intermolecular":[156],"organization.":[157],"A":[158],"Quantum":[159],"Theory":[160],"Atoms":[162],"Molecules":[164],"(QTAIM)":[165],"confirmed":[167,184],"interaction":[171],"through":[172],"corresponding":[174],"critical":[176],"point":[177],"associated":[179],"topological":[180],"descriptors":[181],"also":[183],"secondary":[187],"C\u2014H...N(imine)":[189],"contact":[190],"forms":[191],"nonplanar":[193],"motif.":[196],"FT\u2013IR,":[198],"NMR":[201],"mass":[203],"spectrometric":[204],"data":[205],"support":[206],"proposed":[208],"structure.":[210],"combined":[212],"crystallographic,":[213],"QTAIM":[217],"analyses":[218],"demonstrate":[219],"co-operative":[221],"influence":[222],"bonding":[225],"weak":[227],"noncovalent":[228],"on":[230],"stabilization":[233],"assembly":[236],"this":[238],"system.":[241]},"counts_by_year":[],"updated_date":"2026-11-06T12:05:46.655746","created_date":"2026-09-05T00:00:00"}
