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Volume 69 
Part 12 
Page o1765  
December 2013  

Received 28 October 2013
Accepted 7 November 2013
Online 13 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.137
Data-to-parameter ratio = 17.7
Details
Open access

6-Chloro-N-(pyridin-4-ylmeth­yl)pyridine-3-sulfonamide

aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur Karnataka 572 103, India,bSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India, and cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur Karnataka 572 103, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title sulfonamide derivative, C11H10ClN3O2S, the dihedral angle between the pyridine rings is 46.85 (12)°. The N atom of the chloro­pyridine ring is anti to the N-H bond. In the crystal, mol­ecules are linked through N-H...N hydrogen bonds into zigzag chains parallel to [001] with a C(7) graph-set motif.

Related literature

For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the anti­microbial activity of related compounds, see: Desai et al. (2013[Desai, N. C., Satodiya, H. M., Rajpara, K. M., Joshi, V. V. & Vaghani, H. V. (2013). Indian J. Chem. Sect. B, 52, 904-914.]); Mohan et al. (2013[Mohan, R. N., Sreenivasa, S., Manojkumar, K. E. & Madhu Chakrapani Rao, T. (2013). J. Appl. Chem. 2, 722-729.]). For the proliferation activity of these compounds, see: Renu et al. (2006[Renu, M., Mithu, B., Anasuya, R., Tapas, M., Leslie, W., Takashi, O., Bhabatarak, B. & Dulal, P. (2006). Biochemistry, 45, 5440-5449.]), and for their tuberculostaic acitivity, see: Gobis et al. (2013[Gobis, K., Foks, H., Slawinski, J., Augustynowicz-Kopec, E. & Napiorkowska, A. (2013). Monatsh. Chem. 144, 1197-1203.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10ClN3O2S

  • Mr = 283.73

  • Monoclinic, P 21 /c

  • a = 5.4140 (6) Å

  • b = 18.172 (2) Å

  • c = 12.9392 (15) Å

  • [beta] = 92.388 (6)°

  • V = 1271.9 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.46 mm-1

  • T = 293 K

  • 0.35 × 0.29 × 0.23 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.852, Tmax = 0.899

  • 20929 measured reflections

  • 2961 independent reflections

  • 2185 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.137

  • S = 0.82

  • 2961 reflections

  • 167 parameters

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-HN2...N3i 0.78 (3) 2.10 (3) 2.870 (3) 174.53
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2782 ).


Acknowledgements

The authors thank Prof T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2009). APEX2, SADABS and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Desai, N. C., Satodiya, H. M., Rajpara, K. M., Joshi, V. V. & Vaghani, H. V. (2013). Indian J. Chem. Sect. B, 52, 904-914.
Gobis, K., Foks, H., Slawinski, J., Augustynowicz-Kopec, E. & Napiorkowska, A. (2013). Monatsh. Chem. 144, 1197-1203.  [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Mohan, R. N., Sreenivasa, S., Manojkumar, K. E. & Madhu Chakrapani Rao, T. (2013). J. Appl. Chem. 2, 722-729.
Renu, M., Mithu, B., Anasuya, R., Tapas, M., Leslie, W., Takashi, O., Bhabatarak, B. & Dulal, P. (2006). Biochemistry, 45, 5440-5449.  [Web of Science] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1765  [ doi:10.1107/S1600536813030523 ]

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