Crystal structures of two isomers of 1-(naphthalen-1-yl)ethanol

Crystal structures, Hirshfeld surfaces and energy lattices of (<i>S</i>)-1-(naphthalen-1-yl)ethanol (<b>1</b>) and (<i>R</i>)-1-(naphthalen-2-yl)ethanol (<b>2</b>), both C₁₂H₁₂O, were studied to understand much the lower crystallization propensity of the latter. In both structures, mol-ecules are linked by strong hydrogen bonds into helical chains where Coulombic inter-actions expectedly dominate, but dispersive inter-actions of <b>1</b> and <b>2</b> differ significantly, resulting in large gaps in the total energy lattice of <b>2</b>. The poor crystallization and and higher <i>Z</i>' (4 <i>vs</i> 2 in structure <b>1</b>) of <b>2</b> can be explained by frustration between supra-molecular synthons (⋯O-H⋯O-H⋯ hydrogen-bonding chain <i>vs</i> π-π- inter-actions between naphthalene moieties). The study provides new insights into the supra-molecular inter-actions and crystal packing of regioisomeric naphthalenyl-ethanol compounds, which may have implications for the design of new materials with tailored properties.