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Volume 69 
Part 7 
Page o1170  
July 2013  

Received 6 June 2013
Accepted 25 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.003 Å
R = 0.038
wR = 0.088
Data-to-parameter ratio = 20.7
Details
Open access

4-Bromo-2-[5-methyl-2-(morpholin-4-yl)-1,3-thiazol-4-yl]phenol

aDepartment of Chemistry, "Al. I. Cuza" University Iasi, 11 Carol I Bvd, Iasi 700506, Romania, and bChemisches Institut der Otto-von-Guericke-Universität, Universitätsplatz 2, D-39116 Magdeburg, Germany
Correspondence e-mail: lbirsa@uaic.ro

In the title compound, C14H15BrN2O2S, synthesized by the reaction of the corresponding phenacyl thiocyanate with morpholine, the dihedral angle between the 1,3-thiazole ring and the phenolic substituent ring is 23.46 (10)° as a result of the steric influence of the ortho-methyl group on the thiazole ring. A strong intramolecular phenolic O-H...N hydrogen bond is present in the molecule. In the crystal, a weak C-H...Ophenol hydrogen bond gives rise to chains lying parallel to [20-1]. A short intermolecular Br...Omorpholine interaction is also present [3.1338 (19) Å].

Related literature

For details of the synthesis, see: Seliger et al. (1997[Seliger, H., Happ, E., Cascaval, A., Birsa, M. L. & Novitschi, G. (1997). An. St. Univ. Al. I. Cuza Iasi, 5, 123-128.]). For a recent review on thiazoles, see: Zagade & Senthilkumar (2011[Zagade, A. A. & Senthilkumar, G. P. (2011). Pharma Chem. 3, 523-537.]). For the pharmacological activity and applications of thiazole derivatives, see: Ghaemmaghami et al. (2010[Ghaemmaghami, S., May, B. C. H., Renslo, A. R. & Prusiner, S. B. (2010). J. Virol. 84, 3408-3412.]); Coco & Onnis (1993[Coco, M. T. & Onnis, V. (1993). Synthesis, pp. 199-201.]); Gewald et al. (1994[Gewald, K., Hain, U., Schindler, R. & Gruner, M. (1994). Monatsh. Chem. 125, 1129-1143.]); Tanaka et al. (1994[Tanaka, A., Sakai, H., Motoyama, Y., Ishikawa, T. & Takasugi, H. (1994). J. Med. Chem. 37, 1189-1199.]); Zimmermann et al. (1990[Zimmermann, T., Fischer, G. W., Teller, J., Dehne, H. & Olk, B. (1990). J. Prakt. Chem. 332, 723-730.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15BrN2O2S

  • Mr = 355.25

  • Monoclinic, P 21 /c

  • a = 12.026 (2) Å

  • b = 8.3448 (17) Å

  • c = 14.279 (3) Å

  • [beta] = 91.98 (3)°

  • V = 1432.1 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.02 mm-1

  • T = 153 K

  • 0.60 × 0.50 × 0.50 mm

Data collection
  • Stoe IPDS 2T area-detector diffractometer

  • Absorption correction: for a sphere [modification of the interpolation procedure of Dwiggins (1975[Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.])] Tmin = 0.090, Tmax = 0.117

  • 9876 measured reflections

  • 3848 independent reflections

  • 3258 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.088

  • S = 1.11

  • 3848 reflections

  • 186 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.83 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.88 (4) 1.79 (3) 2.603 (2) 154 (3)
C9-H9C...O1i 0.98 2.47 3.357 (3) 150
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2266 ).


Acknowledgements

Part of this work was supported by a grant of the Romanian National Authority for Scientific Research, CNDI-UEFISCDI, project No. 51/2012.

References

Coco, M. T. & Onnis, V. (1993). Synthesis, pp. 199-201.
Dwiggins, C. W. (1975). Acta Cryst. A31, 146-148.  [CrossRef] [IUCr Journals]
Gewald, K., Hain, U., Schindler, R. & Gruner, M. (1994). Monatsh. Chem. 125, 1129-1143.  [CrossRef] [ChemPort]
Ghaemmaghami, S., May, B. C. H., Renslo, A. R. & Prusiner, S. B. (2010). J. Virol. 84, 3408-3412.  [CrossRef] [ChemPort] [PubMed]
Seliger, H., Happ, E., Cascaval, A., Birsa, M. L. & Novitschi, G. (1997). An. St. Univ. Al. I. Cuza Iasi, 5, 123-128.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.
Tanaka, A., Sakai, H., Motoyama, Y., Ishikawa, T. & Takasugi, H. (1994). J. Med. Chem. 37, 1189-1199.  [CrossRef] [ChemPort] [PubMed]
Zagade, A. A. & Senthilkumar, G. P. (2011). Pharma Chem. 3, 523-537.  [ChemPort]
Zimmermann, T., Fischer, G. W., Teller, J., Dehne, H. & Olk, B. (1990). J. Prakt. Chem. 332, 723-730.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1170  [ doi:10.1107/S1600536813017510 ]

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