engleski

The crystal and molecular structure of (1RS, 2SR)-1-[N-(tert-butoxycarbonyl)amino]-2-hydroxymethylcyclopropane-1-carboxylic acid

1-Aminocyclopropane-1-carboxylic acid (ACC) and its derivatives have been of considerable interest to plant biologist and chemist alike. Because of the unusual coordination of C(alpha) atom, the conformational effects caused by the introduction of ACC residue in polypeptide chain came into the focus of interest, and many peptides containing this residue were prepared and studied. The main structural feature of the title compound is a disordered carboxylic group. It is indicated by the values of the C-O bonds and the corresponding C-C-O angles, which are equal within the limits of two standard error values [C4-O1 = 1.258(3), C4-O2 = 1.263(2) Å ; C1-C4-O1 = 118.6(2), C1-C4-O2 118.3(2)°]. The compound crystallizes as centrosymmetric hydrogen bonded dimer with O1...O2 distance of 2.620(3) Å and O1-H...O2 angle of 168(4)o. Intermolecular hydrogen bond C2...O2 [3.396(3) Å ; 143o] forms a ten-membered ring of the R22(10) type, and consequently a new kind of dimer. Intermolecular hydrogen bond N1...O5 [2.876(3) Å ; 174(2)o] forms infinite chains along the b axis. These chains are additionally connected by a very weak intermolecular hydrogen bond C3...O3 [3.501(3) Å ; 165o] forming two-dimensional networks separated by hydrophobic channels in ab plane.

crystal structure; 1-amino-1-carboxylic acid derivatives; hydrogen bonds

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