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Volume 68 
Part 11 
Pages o3209-o3210  
November 2012  

Received 8 October 2012
Accepted 22 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.008 Å
Disorder in main residue
R = 0.042
wR = 0.103
Data-to-parameter ratio = 13.3
Details
Open access

N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfanyl}-4-methoxyphenyl)benzenesulfonamide

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India,bPG Department of Studies in Chemistry, JSS College of Arts, Commerce and Science, Ooty Road, Mysore 570 025, India, and cX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: mas@physics.uni-mysore.ac.in

The title compound, C22H23BrN4O3S2, crystallizes with two molecules, A and B, in the asymmetric unit. In one of these, the methoxy group is disordered over two sets of sites in a 0.565 (9):0.435 (9) ratio. The benzene rings bridged by the sulfonamide group are tilted relative to each other by 37.4 (1) and 56.1 (1)° in molecules A and B, respectively, while the dihedral angles between the sulfur-bridged pyrimidine and benzene rings are 72.4 (1) and 70.2 (1)° for A and B, respectively. The piperidine ring adopts a chair conformation in both molecules. In the crystal, inversion dimers linked by pairs of N-H...N hydrogen bonds occur for both A and B; the dimers are linked into [010] chains by C-H...O hydrogen bonds. The crystal structure also features inversion-generated aromatic [pi]-[pi] stacking interactions between the pyrimidine rings for both molecules [centroid-centroid distances = 3.412 (2) (molecule A) and 3.396 (2) Å (molecule B)].

Related literature

For the biological activity of sulfonamide compounds, see: Lee et al. (2002[Lee, J. S. & Lee, C. H. (2002). Bull. Korean Chem. Soc. 23, 167-169.]); Laurence (2009[Laurence, M. (2009). East Asia. Sci. Tech. Soc. 3, 257-285.]). For related structures, see: Rodrigues et al. (2011[Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2891.]); Akkurt et al. (2011[Akkurt, M., Mariam, I., Naseer, I., Khan, I. U. & Sharif, S. (2011). Acta Cryst. E67, o186.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Kumar, M., Mallesha, L. & Sridhar, M. A. (2012). Acta Cryst. E68, o2590-o2591.]); Kumar et al. (2012[Kumar, M., Mallesha, L., Sridhar, M. A., Kapoor, K., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o3061.]).

[Scheme 1]

Experimental

Crystal data
  • C22H23BrN4O3S2

  • Mr = 535.47

  • Triclinic, [P \overline 1]

  • a = 13.6081 (6) Å

  • b = 14.5662 (5) Å

  • c = 14.7502 (7) Å

  • [alpha] = 74.439 (4)°

  • [beta] = 69.077 (4)°

  • [gamma] = 62.581 (4)°

  • V = 2405.10 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.91 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.920, Tmax = 1.000

  • 18681 measured reflections

  • 8017 independent reflections

  • 5364 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.103

  • S = 1.02

  • 8017 reflections

  • 601 parameters

  • 35 restraints

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

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N8A-H8A...N20Ai 0.86 2.15 2.940 (4) 152
N8B-H8B...N20Bii 0.78 (4) 2.28 (4) 2.974 (5) 149 (4)
C11A-H11A...O1Aiii 0.93 2.47 3.372 (5) 164
C10B-H10B...O2Biv 0.93 2.60 3.278 (6) 131
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y, -z+2; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y-1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6971 ).


Acknowledgements

MK acknowledges the help of Bahubali College of Engineering, Shravanabelagola, for his research work. RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Akkurt, M., Mariam, I., Naseer, I., Khan, I. U. & Sharif, S. (2011). Acta Cryst. E67, o186.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kant, R., Gupta, V. K., Kapoor, K., Kumar, M., Mallesha, L. & Sridhar, M. A. (2012). Acta Cryst. E68, o2590-o2591.  [CSD] [CrossRef] [details]
Kumar, M., Mallesha, L., Sridhar, M. A., Kapoor, K., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o3061.  [CrossRef] [details]
Laurence, M. (2009). East Asia. Sci. Tech. Soc. 3, 257-285.
Lee, J. S. & Lee, C. H. (2002). Bull. Korean Chem. Soc. 23, 167-169.  [CrossRef] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2891.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3209-o3210   [ doi:10.1107/S1600536812043668 ]

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