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Herein, we demonstrate a brittle\u2010to\u2010elastic transition by subtle molecular modification in a pair of structurally analogous aromatic amides; N\u2010[(4\u2010methoxyphenyl)methyl]formamide (\n                    <jats:bold>N4MFA<\/jats:bold>\n                    ,\n                    <jats:bold>Crystal 1<\/jats:bold>\n                    ) and N\u2010benzylformamide (\n                    <jats:bold>NBFA<\/jats:bold>\n                    ,\n                    <jats:bold>Crystal 2<\/jats:bold>\n                    ). Despite their close structural similarity,\n                    <jats:bold>Crystal 1<\/jats:bold>\n                    exhibits brittle fracture under minimal stress, whereas\n                    <jats:bold>Crystal 2<\/jats:bold>\n                    shows 1D elastic flexibility with reversible bending. Structural, computational, and mechanical analyses reveal that this contrast arises from substituent\u2010controlled supramolecular packing. In\n                    <jats:bold>Crystal 1<\/jats:bold>\n                    , the methoxy (\u2013OCH\n                    <jats:sub>3<\/jats:sub>\n                    ) group promotes dense, anisotropic packing, leading to rigidity and fracture under stress. Removing the substituent in\n                    <jats:bold>Crystal 2<\/jats:bold>\n                    enhances isotropy, \u03c0\u2013\u03c0 stacking, and interlocked packing, enabling reversible strain during elastic bending. Nanoindentation, energy framework, and elastic tensor analyses confirm this transition:\n                    <jats:bold>Crystal 2<\/jats:bold>\n                    shows near\u2010isotropic stiffness (\n                    <jats:italic>E<\/jats:italic>\n                    <jats:sub>max<\/jats:sub>\n                    \/\n                    <jats:italic>E<\/jats:italic>\n                    <jats:sub>min<\/jats:sub>\n                    \u00a0=\u00a01.65) and interconnected energy networks, whereas\n                    <jats:bold>Crystal 1<\/jats:bold>\n                    exhibits pronounced anisotropy (\n                    <jats:italic>E<\/jats:italic>\n                    <jats:sub>max<\/jats:sub>\n                    \/\n                    <jats:italic>E<\/jats:italic>\n                    <jats:sub>min<\/jats:sub>\n                    \u00a0=\u00a03.95) and 1D cohesion. Hirshfeld surface analysis supports more balanced contacts in the elastic crystal. This work establishes a direct structure\u2013mechanical correlation, showing that minor chemical modifications can tune flexibility and provide insights to guide the development of adaptive crystalline materials.\n                  <\/jats:p>","DOI":"10.1002\/asia.70795","type":"journal-article","created":{"date-parts":[[2026,5,24]],"date-time":"2026-05-24T03:17:13Z","timestamp":1779592633000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["From Brittle to Elastic: Substituent Effects on Mechanical Flexibility in Aromatic Amide Crystals"],"prefix":"10.1002","volume":"21","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9392-0708","authenticated-orcid":false,"given":"Aritra","family":"Bhowmik","sequence":"first","affiliation":[{"name":"Physical and Materials Chemistry Division CSIR\u2010National Chemical Laboratory Pune India"},{"name":"Academy of Scientific and Innovative Research (AcSIR) Ghaziabad 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