Received 21 February 2013
In the title compound, C20H19N3O4S, a novel tubulin ligand active against human cancer, the dihedral angle between the pyridine ring and the carbazole ring system is 42.87 (10)°. In the crystal, the molecules are held together by N-HO and C-HO hydrogen bonds into layers, which are assembled into a three-dimensional network via - stacking interactions between inversion-related pyridine rings, with centroid-centroid distances of 3.5101 (12) Å.
For the synthesis and properties of the compound and its derivatives, see Hu et al. (2007). For tubulin as a target for anticancer activity, see Wang et al. (2008); Jackson et al. (2007); Jordan et al. (1991); Mollinedo & Gajate (2003); Wilson et al. (1999); Yvon et al. (1999). For the stability of the temperature controller used for the data collection, see Cosier & Glazer (1986).
Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2469 ).
This work was supported by the National Natural Science Foundation of China (30901840) and the New Teachers' Fund for Doctor Stations, Ministry of Education (20101106120032).
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Hu, L.-X., Li, Z.-R., Wang, Y.-M., Wu, Y.-B., Jiang, J.-D. & Boykin, D. W. (2007). Bioorg. Med. Chem. Lett. 17, 1194-1196.
Jackson, J. R., Patrick, D. R., Dar, M. M. & Huang, P. S. (2007). Nat. Rev. Cancer, 7, 107-117.
Jordan, M. A., Thrower, D. & Wilson, L. (1991). Cancer Res. 51, 2212-2222.
Mollinedo, F. & Gajate, C. (2003). Apoptosis, 8, 413-450.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, Y.-M., Hu, L.-X., Liu, Z.-M., Uou, X.-F., Zhang, S.-H., Qu, J.-R., Li, Z.-R., Li, Y., Kong, W.-J., He, H.-W., Shao, R.-G., Zhang, L.-R., Peng, Z.-G., Boykin, D. W. & Jiang, J.-D. (2008). Clin. Cancer Res. 14, 6218-6227.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Wilson, L., Panda, D. & Jordan, M. A. (1999). Cell Struct. Funct. 24, 329-335.
Yvon, A. M., Wadsworth, P. & Jordan, M. A. (1999). Mol. Biol. Cell, 10, 947-959.