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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 [sigma](C-C) = 0.005 Å
R = 0.083
wR = 0.180
Data-to-parameter ratio = 18.2
Details
Open access

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

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-H...N hydrogen bonds. The dimers are connected via N-H...O hydrogen bonds into a three-dimensional network..

Related literature

For benzothiazole derivatives with anti-tumor activity, see: Brantley et al. (2004[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 et al. (2009[Caleta, I., Kralj, M., Marjanovic, M., Bertosa, B., Tomic, S., Pavlovic, G., Pavelic, K. & Karminski-Zamola, G. (2009). J. Med. Chem. 52, 1744-1756.]); Mortimer et al. (2006[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.]) and for benzothiazolines with anti-tuberculous properties, see: Palmer et al. (1971[Palmer, P. J., Trigg, R. B. & Warrington, J. V. (1971). J. Med. Chem. 14, 248-251.]). For related benzothiazole structures, see: Lynch et al. (2002[Lynch, D. E. (2002). Acta Cryst. E58, o1139-o1141.]); Matkovic-Calogovic et al. (2003[Matkovic-Calogovic, D., Popovic, Z., Tralic-Kulenovic, V., Racanè, L. & Karminski-Zamola, G. (2003). Acta Cryst. C59, o190-o191.]); Lei et al. (2010[Lei, C., Fang, X., Yu, H.-Y., Huang, M.-D. & Wang, J.-D. (2010). Acta Cryst. E66, o914.]).

[Scheme 1]

Experimental

Crystal data
  • C16H19N3O5S

  • Mr = 365.41

  • Monoclinic, P 21 /c

  • a = 16.861 (3) Å

  • b = 11.317 (2) Å

  • c = 9.6484 (19) Å

  • [beta] = 98.94 (3)°

  • V = 1818.7 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Higashi, T. (2000). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.921, Tmax = 0.975

  • 14817 measured reflections

  • 4176 independent reflections

  • 3718 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.083

  • wR(F2) = 0.180

  • S = 1.26

  • 4176 reflections

  • 230 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.86 2.16 3.005 (3) 167
N3-H3...O3ii 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[Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ORTEX (McArdle, 1995[McArdle, P. (1995). J. Appl. Cryst. 28, 65.]); 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.  [CrossRef] [ChemPort]
Caleta, I., Kralj, M., Marjanovic, M., Bertosa, B., Tomic, S., Pavlovic, G., Pavelic, K. & Karminski-Zamola, G. (2009). J. Med. Chem. 52, 1744-1756.  [ISI] [PubMed]
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.  [CrossRef] [details]
Lynch, D. E. (2002). Acta Cryst. E58, o1139-o1141.  [CSD] [CrossRef] [details]
Matkovic-Calogovic, D., Popovic, Z., Tralic-Kulenovic, V., Racanè, L. & Karminski-Zamola, G. (2003). Acta Cryst. C59, o190-o191.  [CSD] [CrossRef] [details]
McArdle, P. (1995). J. Appl. Cryst. 28, 65.  [CrossRef] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Palmer, P. J., Trigg, R. B. & Warrington, J. V. (1971). J. Med. Chem. 14, 248-251.  [CrossRef] [ChemPort] [PubMed] [ISI]
Rigaku (2007). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o115  [ doi:10.1107/S1600536811052421 ]

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