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

Farrukh, M.A.; Mohamed, S.K.; Ahmed, M.; Marzouk, A.A.; El-Moghazy, S.M.

doi:10.1107/S1600536813002134

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 (C-C) = 0.004 Å
R = 0.041
wR = 0.115
Data-to-parameter ratio = 16.0
Details

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

Muhammad A. Farrukh,^a Shaaban K. Mohamed,^b,^c Maqsood Ahmed,^a ^* Adel A. Marzouk ^d and Samir M. El-Moghazy ^e

^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-HN hydrogen bonds lead to the formation of inversion dimers. These dimers are linked via a second pair of N-HN hydrogen bonds and C-HO interactions, forming a two-dimensional network lying parallel to the bc plane. The two-dimensional networks are linked via C-HCl interactions, forming a three-dimensional structure.

Related literature

For the use of pyrazoles in metal-organic chemistry, see: Mukherjee (2000); Halcrow (2009). For the synthesis and pharmaceutical applications of pyrazole compounds, see, for example: Ranatunge et al. (2004); Szabo et al. (2008); Bekhit & Abdel-Aziem (2004); Bekhit et al. (2006); Rostom et al. (2003); Gökhan-Kelekçi et al. (2007); Lin et al. (2007); El-Moghazy et al. (2012); Sakya et al. (2008); Shen et al. (2004).

Experimental

Crystal data

C₁₆H₁₄ClN₃O₂S
M_r = 347.81
Monoclinic, P 2₁ /c
a = 15.878 (5) Å
b = 8.209 (5) Å
c = 12.953 (5) Å
= 91.016 (5)°
V = 1688.1 (13) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.890, T_max = 0.938
17257 measured reflections
3462 independent reflections
2594 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(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
_max = 0.34 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H2N1N3ⁱ	0.82 (2)	2.20 (2)	3.010 (3)	169 (2)
N1-H1N1N3ⁱⁱ	0.84 (3)	2.33 (3)	3.157 (3)	167 (3)
C5-H5O2ⁱⁱⁱ	0.93	2.48	3.169	131
C3-H3Cl1^iv	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

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

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organic compounds