[Journal logo]

Volume 69 
Part 4 
Page o584  
April 2013  

Received 21 February 2013
Accepted 18 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.088
Data-to-parameter ratio = 12.5
Details
Open access

N-(2,6-Dimethoxypyridin-3-yl)-9-methyl-9H-carbazole-3-sulfonamide

aInstitute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Tiantan Xili 1#, Beijing, People's Republic of China
Correspondence e-mail: zongyingliu@263.net

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-H...O and C-H...O hydrogen bonds into layers, which are assembled into a three-dimensional network via [pi]-[pi] stacking interactions between inversion-related pyridine rings, with centroid-centroid distances of 3.5101 (12) Å.

Related literature

For the synthesis and properties of the compound and its derivatives, see Hu et al. (2007[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.]). For tubulin as a target for anticancer activity, see Wang et al. (2008[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.]); Jackson et al. (2007[Jackson, J. R., Patrick, D. R., Dar, M. M. & Huang, P. S. (2007). Nat. Rev. Cancer, 7, 107-117.]); Jordan et al. (1991[Jordan, M. A., Thrower, D. & Wilson, L. (1991). Cancer Res. 51, 2212-2222.]); Mollinedo & Gajate (2003[Mollinedo, F. & Gajate, C. (2003). Apoptosis, 8, 413-450.]); Wilson et al. (1999[Wilson, L., Panda, D. & Jordan, M. A. (1999). Cell Struct. Funct. 24, 329-335.]); Yvon et al. (1999[Yvon, A. M., Wadsworth, P. & Jordan, M. A. (1999). Mol. Biol. Cell, 10, 947-959.]). For the stability of the temperature controller used for the data collection, see Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C20H19N3O4S

  • Mr = 397.45

  • Monoclinic, P 21 /c

  • a = 13.5078 (2) Å

  • b = 7.9272 (1) Å

  • c = 20.9276 (3) Å

  • [beta] = 124.027 (1)°

  • V = 1857.20 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.83 mm-1

  • T = 120 K

  • 0.45 × 0.36 × 0.32 mm

Data collection
  • Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.475, Tmax = 0.556

  • 11460 measured reflections

  • 3280 independent reflections

  • 3161 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.088

  • S = 1.06

  • 3280 reflections

  • 262 parameters

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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.52 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.81 (2) 2.56 (2) 3.3387 (18) 163 (2)
C18-H18A...O1ii 0.96 2.45 3.398 (2) 170
C10-H10...O2iii 0.93 2.56 3.4887 (19) 177
Symmetry codes: (i) x, y+1, z; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2469 ).


Acknowledgements

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).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jordan, M. A., Thrower, D. & Wilson, L. (1991). Cancer Res. 51, 2212-2222.  [ChemPort] [PubMed] [ISI]
Mollinedo, F. & Gajate, C. (2003). Apoptosis, 8, 413-450.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Wilson, L., Panda, D. & Jordan, M. A. (1999). Cell Struct. Funct. 24, 329-335.  [ISI] [CrossRef] [PubMed] [ChemPort]
Yvon, A. M., Wadsworth, P. & Jordan, M. A. (1999). Mol. Biol. Cell, 10, 947-959.  [ISI] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o584  [ doi:10.1107/S1600536813007460 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.