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Volume 66 
Part 2 
Pages o399-o400  
February 2010  

Received 16 December 2009
Accepted 11 January 2010
Online 20 January 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.080
Data-to-parameter ratio = 14.7
Details
Open access

5-Chlorobenzothiazole-2-spiro-3'-indolin-2'-one

aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, stanbul University, 34116 Beyazit-stanbul, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

The title compound, C14H9ClN2OS, crystallizes with two unique molecules, A and B, in the asymmetric unit. The five-membered rings of the benzothiazole groups in both molecules adopt an envelope conformation [puckering parameters: q2 = 0.242 (1) Å and [varphi]2 = 217.5 (4)° for A, and q2 = 0.234 (1) Å and [varphi]2 = 37.7 (4)° for B]. The five-membered rings of the indolinone groups in both molecules are also not planar, with a twisted conformation [puckering parameters are q2 = 0.112 (2) Å and [varphi]2 = 126.3 (8)° for A, and q2 = 0.108 (2) Å and [varphi]2 = 306.4 (9)° for B]. In the crystal structure, there are intermolecular N-H...O, N-H...S and C-H...O hydrogen-bonding interactions, forming the layers propagating normal to c.

Related literature

For general background to and applications of 1H-indole-2,3-dione derivatives, see: Alam & Nawwar (2002[Alam, Y. A. & Nawwar, G. A. M. (2002). Heteroat. Chem. 13, 207-210.]); Cho et al. (2008[Cho, Y., Loerger, T. R. & Sacchettini, J. C. (2008). J. Med. Chem. 51, 5984-5992.]); Da-Silva et al. (2001[Da-Silva, J. F. M., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.]); Dandia et al. (1990[Dandia, A., Khanna, S. & Joshi, K. C. (1990). J. Indian Chem. Soc. 67, 824-826.]); Hall et al. (2009[Hall, M. D., Salam, N. K., Hellawell, J. L., Fales, H. M., Kensler, C. B., Ludwig, J. A., Szakács, G., Hibbs, D. E. & Gottesman, M. M. (2009). J. Med. Chem. 52, 3191-3204.]); Joshi et al. (1990[Joshi, K. C., Dandia, A. & Khanna, S. (1990). Indian J. Chem. Soc. Sect. B, 29, 824-829.]); Kumar et al. (2008[Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2008). J. Med. Chem. 51, 5731-5735.]); Quenelle et al. (2006[Quenelle, D. C., Keith, K. A. & Kern, K. E. R. (2006). Antiviral Res. 71, 24-30.]); Vine et al. (2007[Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931-938.], 2009[Vine, K. L., Matesic, L., Locke, J. M., Ranson, M. & Skropeta, D. (2009). Anti-Cancer Agents Med. Chem. 9, 397-414.]); 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.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9ClN2OS

  • Mr = 288.75

  • Monoclinic, P 21 /c

  • a = 12.8421 (6) Å

  • b = 9.1159 (3) Å

  • c = 22.1553 (9) Å

  • [beta] = 97.051 (3)°

  • V = 2574.1 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.45 mm-1

  • T = 295 K

  • 0.77 × 0.49 × 0.19 mm

Data collection
  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.723, Tmax = 0.919

  • 23976 measured reflections

  • 5271 independent reflections

  • 3987 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.080

  • S = 1.01

  • 5271 reflections

  • 359 parameters

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2i 0.90 (3) 1.95 (3) 2.840 (2) 171 (2)
N2-H2A...S1ii 0.90 (2) 2.61 (2) 3.506 (1) 177 (2)
N3-H3A...O1iii 0.89 (2) 1.99 (2) 2.867 (2) 166 (2)
N4-H4A...S2iv 0.89 (2) 2.63 (2) 3.511 (1) 176 (2)
C3-H3...O1v 0.93 2.53 3.418 (2) 161
Symmetry codes: (i) x, y-1, z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x, y+1, z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) [-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-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2170 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Alam, Y. A. & Nawwar, G. A. M. (2002). Heteroat. Chem. 13, 207-210.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
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]
Cho, Y., Loerger, T. R. & Sacchettini, J. C. (2008). J. Med. Chem. 51, 5984-5992.  [ISI] [CrossRef] [PubMed] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dandia, A., Khanna, S. & Joshi, K. C. (1990). J. Indian Chem. Soc. 67, 824-826.  [ChemPort]
Da-Silva, J. F. M., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.  [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hall, M. D., Salam, N. K., Hellawell, J. L., Fales, H. M., Kensler, C. B., Ludwig, J. A., Szakács, G., Hibbs, D. E. & Gottesman, M. M. (2009). J. Med. Chem. 52, 3191-3204.  [ISI] [CrossRef] [PubMed] [ChemPort]
Joshi, K. C., Dandia, A. & Khanna, S. (1990). Indian J. Chem. Soc. Sect. B, 29, 824-829.
Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2008). J. Med. Chem. 51, 5731-5735.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Quenelle, D. C., Keith, K. A. & Kern, K. E. R. (2006). Antiviral Res. 71, 24-30.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Vine, K. L., Locke, J. M., Ranson, M., Pyne, S. G. & Bremner, J. B. (2007). Bioorg. Med. Chem. 15, 931-938.  [CrossRef] [PubMed] [ChemPort]
Vine, K. L., Matesic, L., Locke, J. M., Ranson, M. & Skropeta, D. (2009). Anti-Cancer Agents Med. Chem. 9, 397-414.  [PubMed] [ChemPort]


Acta Cryst (2010). E66, o399-o400   [ doi:10.1107/S1600536810001285 ]

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