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Volume 66 
Part 8 
Page o2143  
August 2010  

Received 13 July 2010
Accepted 23 July 2010
Online 31 July 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.058
wR = 0.145
Data-to-parameter ratio = 18.8
Details
Open access

Ethyl 2-[4-(1,3-benzothiazol-2-yl)anilino]acetate

aSchool of Chemical and Materials Engineering, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China
Correspondence e-mail: zy0340907@yahoo.com.cn

In the title compound, C17H16N2O2S, the dihedral angle between the benzothiazole ring system and the benzene ring is 1.20 (2)°. The substituted amino substituent is in an extended conformation with an N-C-C-O torsion angle of 179.4 (3)°. In the crystal structure, pairs of molecules are connected by intermolecular N-H...O and weak C-H...O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For background to thioflavin T (ThT), a benzothiazole dye that exhibits enhanced fluorescence upon binding to amyloid fibrils, and its derivatives, see: Kung et al. (2001[Kung, H. F., Lee, C.-W., Zhuang, Z.-P., Kung, M.-P., Hou, C. & Plssl, K. (2001). J. Am. Chem. Soc. 123, 12740-12741.]); Qu et al. (2007[Qu, W., Kung, M.-P., Hou, C., Oya, S. & Kung, H. F. (2007). J. Med. Chem. 50, 3380-3387.]); Zhang & Zhao (2009[Zhang, Y. & Zhao, B. (2009). Acta Cryst. E65, o2762.]). For the synthesis, see: Stephenson et al. (2007[Stephenson, K. A., Chandra, R., Zhuang, Z.-P., Hou, C., Oya, S., Kung, M.-P. & Kung, H. F. (2007). Bioconjugate Chem. 18, 238-246.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16N2O2S

  • Mr = 312.38

  • Monoclinic, P 21 /n

  • a = 5.6303 (1) Å

  • b = 26.1604 (5) Å

  • c = 10.5989 (2) Å

  • [beta] = 98.294 (1)°

  • V = 1544.79 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 298 K

  • 0.36 × 0.24 × 0.21 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.926, Tmax = 0.956

  • 11631 measured reflections

  • 3808 independent reflections

  • 3015 reflections with I > 2[sigma](I)

  • Rint = 0.076

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.145

  • S = 1.07

  • 3808 reflections

  • 203 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...O2i 0.93 2.60 3.390 (2) 144
N2-H2A...O2i 0.85 (1) 2.40 (1) 3.188 (2) 154 (2)
Symmetry code: (i) -x-1, -y, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2007[Bruker (2007). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5087 ).


References

Bruker (2007). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Kung, H. F., Lee, C.-W., Zhuang, Z.-P., Kung, M.-P., Hou, C. & Plssl, K. (2001). J. Am. Chem. Soc. 123, 12740-12741.  [ISI] [CrossRef] [PubMed] [ChemPort]
Qu, W., Kung, M.-P., Hou, C., Oya, S. & Kung, H. F. (2007). J. Med. Chem. 50, 3380-3387.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Stephenson, K. A., Chandra, R., Zhuang, Z.-P., Hou, C., Oya, S., Kung, M.-P. & Kung, H. F. (2007). Bioconjugate Chem. 18, 238-246.  [ISI] [CrossRef] [ChemPort]
Zhang, Y. & Zhao, B. (2009). Acta Cryst. E65, o2762.  [CrossRef] [details]


Acta Cryst (2010). E66, o2143  [ doi:10.1107/S1600536810029442 ]

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