Methyl 2-[2-(tert-but­oxy­carbonyl­amino)-1,3-benzothia­zole-6-carboxamido]­acetate

Gao, D.; Fang, X.; Yu, H.-Y.; Wang, J.-D.

doi:10.1107/S1600536811052421

Volume 68
Part 1
Page o115
January 2012

Received 9 November 2011
Accepted 5 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.083
wR = 0.180
Data-to-parameter ratio = 18.2
Details

Methyl 2-[2-(tert-butoxycarbonylamino)-1,3-benzothiazole-6-carboxamido]acetate

Dan Gao,^a Xing Fang,^a Hai-Yang Yu ^a and Jun-Dong Wang ^a ^*

^aDepartment of Chemistry, University of Fuzhou, Fuzhou 350108, People's Republic of China
Correspondence e-mail: wangjd@fzu.edu.cn

In the title compound, C₁₆H₁₉N₃O₅S, the dihedral angle between the benzene ring and the carbonylamino group is 18.18 (2)°. In the crystal, molecules form centrosymmetric dimers via pairs of N-HN hydrogen bonds. The dimers are connected via N-HO hydrogen bonds into a three-dimensional network..

Related literature

For benzothiazole derivatives with anti-tumor activity, see: Brantley et al. (2004); Caleta et al. (2009); Mortimer et al. (2006) and for benzothiazolines with anti-tuberculous properties, see: Palmer et al. (1971). For related benzothiazole structures, see: Lynch et al. (2002); Matkovic-Calogovic et al. (2003); Lei et al. (2010).

Experimental

Crystal data

C₁₆H₁₉N₃O₅S
M_r = 365.41
Monoclinic, P 2₁ /c
a = 16.861 (3) Å
b = 11.317 (2) Å
c = 9.6484 (19) Å
= 98.94 (3)°
V = 1818.7 (6) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 293 K
0.54 × 0.33 × 0.12 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer
Absorption correction: numerical (NUMABS; Higashi, 2000) T_min = 0.921, T_max = 0.975
14817 measured reflections
4176 independent reflections
3718 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.083
wR(F²) = 0.180
S = 1.26
4176 reflections
230 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N2ⁱ	0.86	2.16	3.005 (3)	167
N3-H3O3ⁱⁱ	0.86	2.11	2.802 (3)	137
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2042 ).

Acknowledgements

The authors gratefully acknowledge financial support from the Foundations of Fuzhou University (Nos. XRC0924, 2010-XQ-06, JA11020).

References

Brantley, E., Trapani, V., Alley, M. C., Hose, C. D., Bradshaw, T. D., Stevens, M. F. G., Sausville, E. A. & Stinson, S. F. (2004). Drug Metab. Disp. 32, 1392-1401.
Caleta, I., Kralj, M., Marjanovic, M., Bertosa, B., Tomic, S., Pavlovic, G., Pavelic, K. & Karminski-Zamola, G. (2009). J. Med. Chem. 52, 1744-1756.
Higashi, T. (2000). NUMABS. Rigaku Corporation, Tokyo, Japan.
Lei, C., Fang, X., Yu, H.-Y., Huang, M.-D. & Wang, J.-D. (2010). Acta Cryst. E66, o914.
Lynch, D. E. (2002). Acta Cryst. E58, o1139-o1141.
Matkovic-Calogovic, D., Popovic, Z., Tralic-Kulenovic, V., Racanè, L. & Karminski-Zamola, G. (2003). Acta Cryst. C59, o190-o191.
McArdle, P. (1995). J. Appl. Cryst. 28, 65.
Mortimer, C. G., Wells, G., Crochard, J., Stone, E. L., Bradshaw, T. D., Stevens, M. F. G. & Westwell, A. D. (2006). J. Med. Chem. 49, 179-185.
Palmer, P. J., Trigg, R. B. & Warrington, J. V. (1971). J. Med. Chem. 14, 248-251.
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds