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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,*
1 Materials Chemistry laboratory, Department of Chemistry, Government College University, Lahore-54000, Pakistan 2 X-ray Diffraction and Crystallography Laboratory, Department of Physics, School of Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore-54590, Pakistan 3 Department of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, Scotland, UK
* Authors to whom correspondence should be addressed.
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 (CC BY 3.0).
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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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