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Reddy DS , Panneerselvam K , Shimoni L , Carrell HL , Desiraju GR
Molecular and Crystal-Structure of 1-(8-Carboxyoctyl)-1,3,5,7- Tetraazaadamantan-1-Ium Bromide and 1-(6-Bromohexyl)-1,3,5,7- Tetraazaadamantan-1-Ium Bromide
Journal of Molecular Structure. 1994 Nov 10;327(2-3) :113-120
PMID: ISI:A1994PR94800003   
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Abstract
The molecular and crystal structures of a pair of quarternised bromide derivatives of hexamethylenetetramine have been determined. 1-(8-Carboxyoctyl)-1,3,5,7-tetraazaadamantan-1-ium bromide, 1, C14H27N4O2Br, M(r) = 363.31, triclinic, P (1) over bar, a = 9.759(5), b = 12.699(7), c = 14.125(6) Angstrom, alpha = 96.45(3), beta = 99.17(3), gamma = 104.74(3)degrees, V = 1649.7(14) Angstrom(3), Z = 4, D-c = 1.463 g cm(-3), lambda(MoK alpha) = 0.7107 Angstrom, mu = 2.503 cm(-1), F(000) = 760, R (on F) = 0.058, R(W) (on I) = 0.162 for 3625 unique reflections with [I > 2 sigma(I)]. There are two symmetry independent sets of ions, each set being linked with strong O...Br interactions to form linear arrays. The symmetry independent arrays are in turn connected with C-H...O interactions to form a layer. 1-(6- Bromohexyl)-1,3,5,7-tetraazaadamantan-1-ium bromide, 2, C12H29N4Br2, M(r) = 384.17, monoclinic, P2(1)/n, a = 8.976(4), b = 15.743(8), c = 11.329(6) Angstrom, beta = 103.70(2)degrees, V = 1555.3(13) Angstrom(3), Z = 4, D-c = 1.641 g cm(-3), lambda(MoK alpha) = 0.7107 Angstrom, mu = 5.203 cm(-1), F(000) = 776, R (on F) = 0.066, R(W) (on I) = 0.168 for 1310 unique non-zero reflections with [I > 2 sigma(I)]. Two Br- anions are located between two cations resulting in the formation of a cyclic centrosymmetric dimer. Each dimer is surrounded by six similar dimers and is connected to them with C-H...N hydrogen bonds to form corrugated molecular sheets. The symmetrical bond lengths of the hexamethylenetetramine skeleton are distorted by quarternisation in both 1 and 2.
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English Article PR948 J MOL STRUCT