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KMID : 0614020020170010016
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Journal of Pharmaceutical Sciences (C.N.U.)
2002 Volume.17 No. 1 p.16 ~ p.27
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Molecular Interaction in Diarylsulfonylimidazolone Crystal-Hydrogen Bond involving C-H Group
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Park Kyung-Lae
Jang Suk-Young
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Abstract
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In the search for a water soluble form of the potential anticancer agent, (S)-(+)-4-Phenyl-1-[1-(4-aminobenzoyl)indoline-5-sulfonyl]-4,5-dihydro-2-imidazolone (I), a series of salt forms were investigated using x-ray single crystal crystallography. The stoichiometrically correct form was found as a 2:1 HCl salt and this HCl salt of the title compound (I) crystallises in space group C2 as [C_24H_22N_4O_4S][C_24H_23N_4O_4S]^+CL^- from a methanol/methylenechloride solution. In this unusual crystal, there are two conformers, which show different structural characteristics. The terminal amine is clearly protonated in the one form with NH_3-Cl distance of 3.110Å, whereas the amine group in the other form is expected to be unprotonated with NH_2-Cl distance of 3.502Å. The role of imidazolone NH group in salt formation is also very peculiar. The imidazolone NH of the two conformers have almost the same distance (3.106Å and 3.103Å) to Cl ion in the crystal packing. In the crystal structure, there are eight distinct hydrogen bonds comprising four N-H…Cl, three N-H…O and one N-H…N, one of which builds bifurcated hydrogen bond with two acceptors sharing one H atom. There exist also one carbonyl oxygen atom accepting two hydrogen atoms. Furthermore, C-H…O contacts assist in the overall hydrogen bonding process.
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KEYWORD
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X-ray, crystal, chirality, H-Bond, conformation, tautomer
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