Abstract
The crystal structure of thiamine iodide sesquihydrate has been determined by X-ray diffraction methods as a host-guest model for coenzyme-substrate interactions. The asymmetric unit contains two chemical units. Both the thiamine molecules A and B, which are crystallographically independent, assume the usualF conformation and have a disordered hydroxyethyl side chain. An iodide anion (or a water molecule) bridges the pyrimidine and thiazolium rings of molecule A (or B) by forming a hydrogen bond with the amino group and an electrostatic contact with the thiazolium ring to stabilize the molecular conformation. In the crystal the thiamine molecules self-associate to form a pipe-like polymeric structure, in which four thiamine hosts surround an iodide guest and hold it through C(2)-H...I hydrogen bonds and thiazolium...I electrostatic interactions. Crystal data: C12H17N4OS+·I− · 1.5 H2O, monoclinic,P21/c, a=12.585(2), b=25.303(5), c=12.030(2) Å, β=115.15(1)°,V=3468(1) Å3,Z=8,D c=1.606 g cm−3,R=0.045 for 3328 observed reflections.
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Supplementary Data relating to this article are deposited with the British Library as Supplementary Publication No. SUP. 82156 (13 pages).
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Ning-Haihu, Zhang, SL. Host-guest interactions of thiamine with anions. Crystal structure ofthiamine iodide sesquihydrate. J Incl Phenom Macrocycl Chem 16, 273–281 (1993). https://doi.org/10.1007/BF00708797
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DOI: https://doi.org/10.1007/BF00708797