Journal of Chemical Crystallography p. 723 - 729 (2005)
Update date:2022-08-22
Topics:
Zeller, Matthias
Wilcox, Robert J.
Snyder III, Floyd G.
Seibel II, Harry A.
Takas, Nathan J.
Hunter, Allen D.
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) A, 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) A and Z = 4. Both compounds show hydrogen bonding in the solid state, forming infinite chains via N-H...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...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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