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Vanillylformamide [systematic name: N-(4-hy­droxy-3-meth­oxy­benz­yl)form­amide], C9H11NO3, (II), has been synthesized from vanillyl­amine hydro­chloride and studied by single-crystal X-ray diffraction. Compound (II) and the well known biologically active eugenol compound (I) can be considered to be `isosteres' of each other, since they share comparable mol­ecular shape and volume. The product (II) crystallizes in the space group P1. In the crystal, the vanillylformamide mol­ecules are linked mainly by N—H⋯O, O—H⋯O and Csp2—H⋯O hydrogen bonds, forming infinite two-dimensional polar sheets. These two-dimensional layers pack in a parallel fashion, constructing a polar three-dimensional network. Except for van der Waals forces and weak Csp3—H⋯O hydrogen bonds, there are no significant inter­mol­ecular inter­actions between the layers. A Cambridge Structural Database search revealed that vanillyl­amide-related crystals are scarce.

Polar crystal of vanillylformamide through replacement of the alkene by an isosteric formamide group