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

Zhang, Y.; Qu, Y.; Zhao, B.

doi:10.1107/S1600536810029442

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 (C-C) = 0.003 Å
R = 0.058
wR = 0.145
Data-to-parameter ratio = 18.8
Details

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

Yong Zhang,^a ^* Yuan Qu ^a and Bi-lin Zhao ^a

^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-HO and weak C-HO 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); Qu et al. (2007); Zhang & Zhao (2009). For the synthesis, see: Stephenson et al. (2007).

Experimental

Crystal data

C₁₇H₁₆N₂O₂S
M_r = 312.38
Monoclinic, P 2₁ /n
a = 5.6303 (1) Å
b = 26.1604 (5) Å
c = 10.5989 (2) Å
= 98.294 (1)°
V = 1544.79 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.926, T_max = 0.956
11631 measured reflections
3808 independent reflections
3015 reflections with I > 2(I)
R_int = 0.076

Refinement

R[F² > 2(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
_max = 0.39 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O2ⁱ	0.93	2.60	3.390 (2)	144
N2-H2AO2ⁱ	0.85 (1)	2.40 (1)	3.188 (2)	154 (2)
Symmetry code: (i) -x-1, -y, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
Qu, W., Kung, M.-P., Hou, C., Oya, S. & Kung, H. F. (2007). J. Med. Chem. 50, 3380-3387.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stephenson, K. A., Chandra, R., Zhuang, Z.-P., Hou, C., Oya, S., Kung, M.-P. & Kung, H. F. (2007). Bioconjugate Chem. 18, 238-246.
Zhang, Y. & Zhao, B. (2009). Acta Cryst. E65, o2762.

organic compounds