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Crystals 2011, 1(2), 69-77; doi:10.3390/cryst1020069
Article

Structures of Benzenesulfonylamino-3-(4-benzenesulfonyloxy-phenyl)-propionic acid and 2-(toluene-4-sulfonylamino)-3-[4-(toluene-4-sulponyl-oxy)-phenyl]-propionic acid: Variations in L-tyrosine Backbone Conformation, Intramolecular Aromatic π–π Stacking and Short C–H···O Interactions

1,* , 1,* , 1, 2 and 3,*
Received: 26 April 2011 / Revised: 8 June 2011 / Accepted: 10 June 2011 / Published: 14 June 2011
(This article belongs to the Special Issue Feature Paper)
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Abstract

The syntheses and crystal structures of benzenesulfonylamino-3-(4-benzenesulfonyloxy-phenyl)-propionic acid (1) and 2-(toluene-4-sulfonylamino)-3-[4-(toluene-4-sulponyloxy)-phenyl]-propionic acid (2) are described. The L-tyrosine cores of the molecules show significant conformational differences. In 1, both organic molecules show intramolecular aromatic π–π stacking and in 2 a very short intermolecular Cα–H···O interaction is seen. The structures of 1 and 2 are compared with those of related materials. Crystal data: 12·H2O·MeOH [2(C21H19NO7S2)·H2O·CH4O], Mr = 973.04, monoclinic, P21 (No. 4), a = 8.0078 (4) Å, b = 34.0704 (16) Å, c = 8.5506 (3) Å, β = 94.239 (3)°, V = 2326.47 (18) Å3, Z = 2, T = 296 K, R(F) = 0.062, wR(F2) = 0.157, 2·H2O (C23H25NO7S2·H2O), Mr = 507.56, monoclinic, P21 (No. 4), a = 5.7171 (7) Å, b = 24.359 (3) Å, c = 9.1043 (10) Å, β = 104.563 (6)°, V = 1227.2 (2) Å3, Z = 2, T = 296 K, R(F) = 0.055, wR(F2) = 0.092.
Keywords: L-tyrosine; green chemistry; torsion angles; C–H···O interactions L-tyrosine; green chemistry; torsion angles; C–H···O interactions
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Khan, M.H.; Khan, I.U.; Arshad, M.N.; Rafique, H.M.; Harrison, W.T.A. Structures of Benzenesulfonylamino-3-(4-benzenesulfonyloxy-phenyl)-propionic acid and 2-(toluene-4-sulfonylamino)-3-[4-(toluene-4-sulponyl-oxy)-phenyl]-propionic acid: Variations in L-tyrosine Backbone Conformation, Intramolecular Aromatic π–π Stacking and Short C–H···O Interactions. Crystals 2011, 1, 69-77.

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