[Journal logo]

Volume 69 
Part 2 
Pages o295-o296  
February 2013  

Received 13 January 2013
Accepted 22 January 2013
Online 26 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.115
Data-to-parameter ratio = 16.0
Details
Open access

4-[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]benzenesulfonamide

aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan,bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England,cChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt,dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, and eFaculty of Pharmacy, Pharmaceutical Chemistry Department, Cairo University, Cairo, Egypt
Correspondence e-mail: maqsood.ahmed@gcu.edu.pk

In the title compound, C16H14ClN3O2S, the dihedral angle between the benzene and pyrazole rings is 52.75 (2)°, while that between the pyrazole and 4-chlorophenyl rings is 54.0 (3)°. The terminal sulfonamide group adopts an approximately tetrahedral geometry about the S atom with a C-S-N angle of 108.33 (10)°. In the crystal, pairs of N-H...N hydrogen bonds lead to the formation of inversion dimers. These dimers are linked via a second pair of N-H...N hydrogen bonds and C-H...O interactions, forming a two-dimensional network lying parallel to the bc plane. The two-dimensional networks are linked via C-H...Cl interactions, forming a three-dimensional structure.

Related literature

For the use of pyrazoles in metal-organic chemistry, see: Mukherjee (2000[Mukherjee, R. (2000). Coord. Chem. Rev. 203, 151-218.]); Halcrow (2009[Halcrow, M. A. (2009). Dalton Trans. pp. 2059-2073.]). For the synthesis and pharmaceutical applications of pyrazole compounds, see, for example: Ranatunge et al. (2004[Ranatunge, R. R., Earl, R. A., Garvey, D. S., Janero, D. R., Letts, L. G., Martino, A. M., Murty, M. G., Richardson, S. K., Schwalb, D. J., Young, D. V. & Zemtseva, I. S. (2004). Bioorg. Med. Chem. Lett. 14, 6049-6052.]); Szabo et al. (2008[Szabo, G., Fischer, J., Kis-Varga, A. & Gyires, K. (2008). J. Med. Chem. 51, 142-147.]); Bekhit & Abdel-Aziem (2004[Bekhit, A. A. & Abdel-Aziem, T. (2004). Bioorg. Med. Chem. 12, 1935-1945.]); Bekhit et al. (2006[Bekhit, A. A., Abdel-Rahman, H. M. & Guemel, A. A. (2006). Arch. Pharm. Chem. Life Sci. 339, 81-87.]); Rostom et al. (2003[Rostom, S. A. F., Shalaby, M. A. & El-Demellawy, M. A. (2003). Eur. J. Med. Chem. 38, 959-974.]); Gökhan-Kelekçi et al. (2007[Gökhan-Kelekçi, N., Yabanoglu, S., Küpeli, E., Salgin, U., Özgen, Ö., Uçar, G., Yesilada, E., Kendi, E., Yesilada, A. & Bilgin, A. A. (2007). Bioorg. Med. Chem. 15, 5775-5786.]); Lin et al. (2007[Lin, R., Chiu, G., Yu, Y., Connolly, P. J., Li, S., Lu, Y., Adams, M., Fuentes-Pesquera, A. R., Emanuel, S. L. & Greenberger, L. M. (2007). Bioorg. Med. Chem. Lett. 17, 4557-4561.]); El-Moghazy et al. (2012[El-Moghazy, S. M., Barsoum, F. F., Abdel-Rahman, H. M. & Marzouk, A. A. (2012). Med. Chem. Res. 21, 1722-1733.]); Sakya et al. (2008[Sakya, S. M., Shavnya, A., Cheng, H., Rast, C. L. B., Li, J., Koss, D. A., Jaynes, B. H., Mann, D. W., Petras, C. F., Seibel, S. B., Haven, M. L. & Lynch, M. P. (2008). Bioorg. Med. Chem. Lett. 18, 1042-1045.]); Shen et al. (2004[Shen, D. M., Shu, M., Mills, S. G., Chapman, K. T., Malkowitz, L., Springer, M. S., Gould, S. L., DeMartino, J. A., Siciliano, S. J., Kwei, G. Y., Carella, A., Carver, G., Holmes, K., Schleif, W. A., Danzeisen, R., Hazuda, D., Kessler, J., Lineberger, J., Miller, M. D. & Emini, E. A. (2004). Bioorg. Med. Chem. Lett. 14, 935-939.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14ClN3O2S

  • Mr = 347.81

  • Monoclinic, P 21 /c

  • a = 15.878 (5) Å

  • b = 8.209 (5) Å

  • c = 12.953 (5) Å

  • [beta] = 91.016 (5)°

  • V = 1688.1 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 296 K

  • 0.33 × 0.32 × 0.18 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: analytical (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.890, Tmax = 0.938

  • 17257 measured reflections

  • 3462 independent reflections

  • 2594 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.115

  • S = 1.03

  • 3462 reflections

  • 217 parameters

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

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H2N1...N3i 0.82 (2) 2.20 (2) 3.010 (3) 169 (2)
N1-H1N1...N3ii 0.84 (3) 2.33 (3) 3.157 (3) 167 (3)
C5-H5...O2iii 0.93 2.48 3.169 131
C3-H3...Cl1iv 0.93 2.93 3.602 130
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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: 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: SJ5296 ).


Acknowledgements

GC University is gratefully acknowledged for use of the X-ray diffraction facility. The authors are also thankful to Manchester Metropolitan University and Alazhar University for supporting this study.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bekhit, A. A. & Abdel-Aziem, T. (2004). Bioorg. Med. Chem. 12, 1935-1945.  [CrossRef] [PubMed] [ChemPort]
Bekhit, A. A., Abdel-Rahman, H. M. & Guemel, A. A. (2006). Arch. Pharm. Chem. Life Sci. 339, 81-87.  [CrossRef] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Moghazy, S. M., Barsoum, F. F., Abdel-Rahman, H. M. & Marzouk, A. A. (2012). Med. Chem. Res. 21, 1722-1733.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gökhan-Kelekçi, N., Yabanoglu, S., Küpeli, E., Salgin, U., Özgen, Ö., Uçar, G., Yesilada, E., Kendi, E., Yesilada, A. & Bilgin, A. A. (2007). Bioorg. Med. Chem. 15, 5775-5786.  [PubMed]
Halcrow, M. A. (2009). Dalton Trans. pp. 2059-2073.  [CrossRef]
Lin, R., Chiu, G., Yu, Y., Connolly, P. J., Li, S., Lu, Y., Adams, M., Fuentes-Pesquera, A. R., Emanuel, S. L. & Greenberger, L. M. (2007). Bioorg. Med. Chem. Lett. 17, 4557-4561.  [CrossRef] [PubMed] [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.  [ISI] [CrossRef] [ChemPort] [details]
Mukherjee, R. (2000). Coord. Chem. Rev. 203, 151-218.  [ISI] [CrossRef] [ChemPort]
Ranatunge, R. R., Earl, R. A., Garvey, D. S., Janero, D. R., Letts, L. G., Martino, A. M., Murty, M. G., Richardson, S. K., Schwalb, D. J., Young, D. V. & Zemtseva, I. S. (2004). Bioorg. Med. Chem. Lett. 14, 6049-6052.  [CrossRef] [PubMed] [ChemPort]
Rostom, S. A. F., Shalaby, M. A. & El-Demellawy, M. A. (2003). Eur. J. Med. Chem. 38, 959-974.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sakya, S. M., Shavnya, A., Cheng, H., Rast, C. L. B., Li, J., Koss, D. A., Jaynes, B. H., Mann, D. W., Petras, C. F., Seibel, S. B., Haven, M. L. & Lynch, M. P. (2008). Bioorg. Med. Chem. Lett. 18, 1042-1045.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shen, D. M., Shu, M., Mills, S. G., Chapman, K. T., Malkowitz, L., Springer, M. S., Gould, S. L., DeMartino, J. A., Siciliano, S. J., Kwei, G. Y., Carella, A., Carver, G., Holmes, K., Schleif, W. A., Danzeisen, R., Hazuda, D., Kessler, J., Lineberger, J., Miller, M. D. & Emini, E. A. (2004). Bioorg. Med. Chem. Lett. 14, 935-939.  [CrossRef] [PubMed] [ChemPort]
Szabo, G., Fischer, J., Kis-Varga, A. & Gyires, K. (2008). J. Med. Chem. 51, 142-147.  [ISI] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o295-o296   [ doi:10.1107/S1600536813002134 ]

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.