Acta Crystallographica Section E (Aug 2013)

2-[(1,3-Benzothiazol-2-yl)iminomethyl]-6-methoxyphenol: a new monoclinic polymorph

  • Edward R. T. Tiekink,
  • Siti Nadiah Binti Abdul Halim,
  • Md. Abdus Salam,
  • Philip G. Jessop,
  • Md. Abu Affan

DOI
https://doi.org/10.1107/S1600536813019387
Journal volume & issue
Vol. 69, no. 8
pp. o1273 – o1273

Abstract

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The title compound, C15H12N2O2S, is a P21/c polymorph of a previously reported P21/n polymorph [Büyükgüngör et al. (2004). Acta Cryst. E60, o1414–o1416]. The dihedral angle between the benzothiazole (r.m.s. deviation = 0.010 Å) and the benzene ring of 7.86 (6)° compares with 10.76 (10)° in the literature structure. The methoxy substituent is almost coplanar with the benzene ring to which it is attached [C—O—C—C torsion angle = 178.31 (14)°] and the conformation about the imine bond [1.287 (2) Å] is E. There is an intramolecular O—H...N hydrogen bond and the hydroxy O and thioether S atoms are syn. In the crystal, columns are formed along the b axis as centrosymmetric dimeric aggregates, mediated by C—H...O interactions and linked by π–π interactions between the thiazole and benzene rings [centroid-to-centroid distance = 3.8256 (10) Å].