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Volume 69 
Part 8 
Page o1273  
August 2013  

Received 13 July 2013
Accepted 13 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.095
Data-to-parameter ratio = 16.3
Details
Open access

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

aDepartment of Chemistry, Queen's University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada,bFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samaharan, Sawarak, Malaysia, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: Edward.Tiekink@gmail.com

The title compound, C15H12N2O2S, is a P21/c polymorph of a previously reported P21/n polymorph [Büyükgüngör et al. (2004[Büyükgüngör, O., Çaliskan, N., Davran, C. & Bati, H. (2004). Acta Cryst. E60, o1414-o1416.]). 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 [pi]-[pi] interactions between the thiazole and benzene rings [centroid-to-centroid distance = 3.8256 (10) Å].

Related literature

For background to the biological activity of organotin compounds with N-, O- and S-atom donors, see: Affan et al. (2009[Affan, M. A., Foo, S. W., Jusoh, I., Hanapi, S. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 5031-5037.]). For the structure of the P21/n polymorph, see: Büyükgüngör et al. (2004[Büyükgüngör, O., Çaliskan, N., Davran, C. & Bati, H. (2004). Acta Cryst. E60, o1414-o1416.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O2S

  • Mr = 284.33

  • Monoclinic, P 21 /c

  • a = 11.6697 (11) Å

  • b = 6.0250 (6) Å

  • c = 18.6441 (18) Å

  • [beta] = 94.346 (1)°

  • V = 1307.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 100 K

  • 0.20 × 0.16 × 0.15 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.669, Tmax = 0.746

  • 15750 measured reflections

  • 2983 independent reflections

  • 2404 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.095

  • S = 1.05

  • 2983 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...N2 0.84 1.88 2.6167 (17) 146
C6-H6...O2i 0.95 2.56 3.424 (2) 151
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), QMol (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2623 ).


Acknowledgements

The authors thank the Natural Sciences and Engineering Council of Canada for support. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (grant No. UM.C/HIR-MOHE/SC/03).

References

Affan, M. A., Foo, S. W., Jusoh, I., Hanapi, S. & Tiekink, E. R. T. (2009). Inorg. Chim. Acta, 362, 5031-5037.  [Web of Science] [CSD] [CrossRef]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Büyükgüngör, O., Çaliskan, N., Davran, C. & Bati, H. (2004). Acta Cryst. E60, o1414-o1416.  [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1273  [ doi:10.1107/S1600536813019387 ]

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