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Volume 68 
Part 4 
Pages o1086-o1087  
April 2012  

Received 8 March 2012
Accepted 9 March 2012
Online 17 March 2012

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Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.006 Å
R = 0.069
wR = 0.179
Data-to-parameter ratio = 15.8
Details
Open access

1-(4-Methylphenyl)-3-phenyl-1H-pyrazol-5-yl 4-nitrobenzenesulfonate

Solange M. S. V. Wardell,a Edward R. T. Tiekinkb* and James L. Wardellc+

aCHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland,bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil
Correspondence e-mail: edward.tiekink@gmail.com

In the title molecule, C22H17N3O5S, the pyrazole ring is planar (r.m.s. deviation = 0.018 Å) and forms dihedral angles of 21.45 (10) and 6.96 (10)° with the N- and C-bound benzene rings, respectively. Supramolecular layers in the bc plane are formed in the crystal via C-H...O and [pi]-[pi] interactions involving the sulfonamide benzene ring interacting with the N- and C-bound benzene rings [centroid-centroid distances = 3.790 (2) and 3.730 (2) Å, respectively]. The crystal studied was found to be a merohedral twin (twin law 1 0 0.678, 0 -1 0, 0 0 -1), the fractional contribution of the minor component being approximately 36%.

Related literature

For related structures and background references to pyrazoles, see: Wardell et al. (2012[Wardell, S. M. S. V., Howie, A. H., Tiekink, E. R. T. & Wardell, J. L. (2012). Acta Cryst. E68, o992-o993.]); Baddeley et al. (2012[Baddeley, T. C., Wardell, S. M. S. V., Tiekink, E. R. T. & Wardell, J. L. (2012). Acta Cryst. E68, o1016-o1017.]). For the synthesis, see: Galoyan et al. (1969[Galoyan, G. A., Agbalyan, S. G. & Esayan, G. T. (1969). Arm. Khim. Zhur. 22, 430-433.]). For the treatment of twinned diffraction data, see: Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

[Scheme 1]

Experimental

Crystal data

  • C22H17N3O5S

  • Mr = 435.46

  • Monoclinic, P 21 /c

  • a = 13.5339 (12) Å

  • b = 10.4827 (10) Å

  • c = 14.9303 (13) Å

  • [beta] = 111.975 (3)°

  • V = 1964.3 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 120 K

  • 0.58 × 0.38 × 0.04 mm
Data collection

  • Rigaku Saturn724+ diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.620, Tmax = 0.746

  • 4454 measured reflections

  • 4454 independent reflections

  • 3951 reflections with I > 2[sigma](I)
Refinement

  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.179

  • S = 1.19

  • 4454 reflections

  • 282 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.62 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5...O4i 0.95 2.50 3.387 (5) 155
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Hooft, 1998[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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: HB6674 ).

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR/MOHE/SC/12) is gratefully acknowledged.

References

Baddeley, T. C., Wardell, S. M. S. V., Tiekink, E. R. T. & Wardell, J. L. (2012). Acta Cryst. E68, o1016-o1017.  [CrossRef] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Galoyan, G. A., Agbalyan, S. G. & Esayan, G. T. (1969). Arm. Khim. Zhur. 22, 430-433.  [ChemPort]
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wardell, S. M. S. V., Howie, A. H., Tiekink, E. R. T. & Wardell, J. L. (2012). Acta Cryst. E68, o992-o993.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2012). E68, o1086-o1087   [ doi:10.1107/S1600536812010598 ]

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