Acta Crystallographica Section C

Crystal Structure Communications

Volume 58, Part 3 (March 2002)

Acta Cryst. (2002). C58, o151-o153 [doi:10.1107/S0108270102000598]

Flat versus twisted rotamers of 2,4-disubstituted thiazoles: the effect of intermolecular hydrogen bonds

S. Bernès, M. I. Berros, C. Rodríguez de Barbarín and F. Sánchez-Viesca

Abstract: In the title compounds, 2-amino-4-(2-chloro-4,5-dimethoxyphenyl)-1,3-thiazole, C₁₁H₁₁ClN₂O₂S, (I), and 4-(2-chloro-4,5-dimethoxyphenyl)-2-methyl-1,3-thiazole, C₁₂H₁₂ClNO₂S, (II), the dihedral angles between the thiazole moiety and the chloroaryl group are 51.61 (10) and 8.44 (14)°, respectively. This difference is a consequence of intermolecular hydrogen bonds forcing the stabilization of a twisted rotamer in (I). Substitution of the amino function by a methyl group precludes these contacts, giving a flat rotamer in (II).

Formula: C₁₁H₁₁ClN₂O₂S and C₁₂H₁₂ClNO₂S

Online 13 February 2002


	Structure factor file (CIF format) (135.3 kbytes) Contains datablock I

	Structure factor file (CIF format) (107.4 kbytes) Contains datablock II

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