The solid state structures of two p-substituted aromatic formamides have been determined. p-Nitro formamido benzene (1) crystallizes in the monoclinic space group C2/c with a = 10.9859(7), b = 10.0576(7), c = 13.0331(9) Å, β = 97.148(1)∘ and Z = 8. p-formamido anisole (2) crystallizes in the orthorhombic space group Pna21 with a = 10.5598(7), b = 7.6553(5), c = 9.2522(6) Å and Z = 4. Both compounds show hydrogen bonding in the solid state, forming infinite chains via N–H⋅ < eqid1 > ⋅O = C bridges. For the anisole formamide (2), the molecules exhibit in a zig-zag arrangement. The nitro compound (1) exhibits a spiral-like wavy line with a fourfold repeating unit, making it the first formamide having a chiral N–H⋅ < eqid2 > ⋅O bridged chain reminiscent of those found for α-helices in proteins. While the individual spirals of 1 are orientated either clockwise or counterclockwise, their orientation towards each other is random.
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Zeller, M., Wilcox, R.J., Snyder, F.G. et al. Hydrogen bonding in aromatic formamides. J Chem Crystallogr 35, 723–729 (2005). https://doi.org/10.1007/s10870-005-6269-3
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DOI: https://doi.org/10.1007/s10870-005-6269-3