J. Wardell, E. Tiekink
May 12, 2011
Citations
1
Influential Citations
19
Citations
Journal
Journal of Chemical Crystallography
Abstract
The eight-membered {···HOC=O}2 synthon featured in the crystal structure of 2-amino-4-nitrobenzoic acid (1) is replaced by carboxylic acid···N-pyridine hydrogen bonds in its cocrystals with 2,2′-bipyridine (2/1; 2) and bis(pyridin-2-yl)ketone (1/1; 3) indicating the robust nature of the latter synthon. Disruption of the three-dimensional architecture based on O–H···O and N–H···O(nitro) hydrogen bonds in (1) is evident in the cocrystals which form supramolecular tubes (2) and chains (3) based on O–H···N and N–H···O hydrogen bonding. Compound (1) crystallizes in the monoclinic space group P21/n with a = 3.6291(1) Å, b = 7.7339(3) Å, c = 26.561(1) Å, β = 91.385(2)°, and Z = 4. Compound (2) crystallizes in the monoclinic space group C2/c with a = 27.562(3) Å, b = 6.8300(6) Å, c = 12.923(1) Å, β = 110.593(5)°, and Z = 4. Compound (3) crystallizes in the monoclinic space group P21/c with a = 3.795(3) Å, b = 12.024(8) Å, c = 35.65(2) Å, β = 92.131(6)°, and Z = 4 (determined from synchrotron data).Graphical AbstractThe carboxylic acid dimer synthon formed in the acid no longer exists in its cocrystals owing to carboxylic acid-OH···N-pyridine interactions. Based on hydrogen bonding a supramolecular tube is formed in the 2/1 cocrystal with 2,2′-bipyridine.