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Here, we demonstrate that structural water acts as a symmetry\u2010breaking and frustration\u2010generating element in artificial self\u2010assembly. Using an asymmetric achiral naphthalene derivative (\n                    <jats:bold>N1<\/jats:bold>\n                    ) as a model system, we show that trace water fundamentally redirects its assembly pathway. In the presence of structural water,\n                    <jats:bold>N1<\/jats:bold>\n                    forms racemic P\/M helical fibers, whereas only non\u2010helical aggregates are obtained under anhydrous conditions or with control molecules lacking sufficient hydrogen\u2010bonding capability. Single\u2010crystal x\u2010ray analysis reveals that each water molecule functions as a tetravalent hydrogen\u2010bonding node, bridging four\n                    <jats:bold>N1<\/jats:bold>\n                    molecules into a nonplanar\n                    <jats:italic>\n                      C\n                      <jats:sub>2<\/jats:sub>\n                    <\/jats:italic>\n                    \u2010symmetric tetramer. This water\u2010centered motif introduces geometric incompatibility with optimal \u03c0\u2013\u03c0 stacking, generating packing frustration that is relieved through hierarchical helical twisting. The hydrogen\u2010bonding network can be reversibly modulated by acid\u2013base stimuli, enabling interconversion between helical and non\u2010helical morphologies. Moreover, the resulting helices can be biased into homochiral states by chiral aromatic amino acids, revealing a water\u2010gated chirality transfer mechanism that is absent under anhydrous conditions. This work extends design principles for supramolecular helicity beyond conventional symmetric monomers and highlights the role of structural water in controlling complex self\u2010assembly pathways.\n                  <\/jats:p>","DOI":"10.1002\/anie.9135596","type":"journal-article","created":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T11:23:11Z","timestamp":1786188191000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Structural Water\u2010Enabled Helicity Emergence From an Asymmetric Achiral Molecule"],"prefix":"10.1002","volume":"65","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8519-8578","authenticated-orcid":false,"given":"Hao","family":"Kong","sequence":"first","affiliation":[{"name":"State Key Laboratory of Chemical Resource Engineering Beijing University of Chemical Technology  Beijing P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2765-1893","authenticated-orcid":false,"given":"Zhen","family":"Wu","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemical Resource Engineering Beijing University of Chemical Technology  Beijing P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bijun","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemical Resource Engineering Beijing University of Chemical Technology  Beijing P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuqian","family":"Jiang","sequence":"additional","affiliation":[{"name":"National Center for Nanoscience and Technology  Beijing P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun","family":"Guan","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemical Resource Engineering Beijing University of Chemical Technology  Beijing P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6603-1251","authenticated-orcid":false,"given":"Minghua","family":"Liu","sequence":"additional","affiliation":[{"name":"Beijing National Laboratory For Molecular Science, CAS Key Laboratory of Colloid, Interface and Chemical Thermodynamics, Institute of Chemistry Chinese Academy of Sciences  Beijing P. R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Meizhen","family":"Yin","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Chemical Resource Engineering Beijing University of Chemical Technology  Beijing P. R. 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