Naslov
Hydrogen bonds in the crystal packings of mesalazine and mesalazine hydrochloride

Autori
Banić-Tomišić, Zrinka ; Kojić-Prodić, Biserka ; Širola, Igor

Izvornik
Journal of molecular structure (0022-2860) 416 (1997), 1-3; 209-220

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
bacteriostatic; X-ray crystallography; mesalazine crystal structure; hydrogen bonds

Sažetak
The crystal structures of pharmaceutical product mesalazine (marketed also under different proprietary names as Salofalk, Asacol, Asacolitin, and Claversal) and its hydrochloride are reported. In the crystal mesalazine is in zwitterion form as 5-ammoniosalicylate (1) whereas mesalazine hydrochloride crystallizes in an ionized form as 5-ammoniosalicylium chloride (2), Compound 1 (C7H7O3N) crystallizes in the monoclinic space group P2(1)/n with a=3.769(1) Angstrom, b=7.353(2) Angstrom, c=23.475(5) Angstrom, beta=94.38(2)degrees, V=648.7(8) Angstrom(3), Z=4, D-c=1.568 g cm(-3) and mu(MoK alpha)=1.2 cm(-1). Compound 2 (C7H8O3NCl) crystallizes in the triclinic space group P (1) over bar with a=4.4839(2) Angstrom, b=5.7936(2) Angstrom, c=15.6819(5) Angstrom, alpha=81.329(3)degrees, beta=88.026(3)degrees, gamma=79.317(4)degrees, V=395.74(3) Angstrom(3), Z=2, D-c=1.591 g cm(-3) and mu(CuK alpha)=40.8 cm(-1). The crystal structures were solved by direct methods and refined to R=0.041 for 1 and 0.028 for 2, using 607 and 1374 observed reflections, respectively. The configuration of both molecules, with the ortho hydroxyl to a carboxyl group, favours the intramolecular hydrogen bonds. Very complex systems of intermolecular hydrogen bonds were observed in both crystal packings. They are discussed in terms of graph-set notation. The mesalazine crystal structure is characterized by two-dimensional network of hydrogen bonds in the ab plane. The crystal structure pattern of mesalazine hydrochloride is a three-dimensional network significantly supported by N+-H ... Cl- interactions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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