[Journal logo]

Volume 68 
Part 11 
Page o3061  
November 2012  

Received 25 September 2012
Accepted 27 September 2012
Online 3 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.046
wR = 0.105
Data-to-parameter ratio = 15.6
Details
Open access

N-[2-(5-Bromo-2-morpholin-4-ylpyrimidin-4-ylsulfanyl)-4-methoxyphenyl]-2,4,6-trimethylbenzenesulfonamide

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

In the title compound, C24H27BrN4O4S2, the molecule is twisted at the sulfonyl S atom with a C-S(O2)-N(H)-C torsion angle of 62.6 (3)°. The benzene rings bridged by the sulfonamide group are tilted to each other by a dihedral angle of 60.6 (1)°. The dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 62.7 (1)°. The morpholine ring adopts a chair conformation. The molecular conformation is stabilized by a weak intramolecular [pi]-[pi] stacking interaction between the pyrimidine and the 2,4,6-trimethylbenzene rings [centroid-centroid distance = 3.793 (2) Å]. In the crystal, molecules are linked by N-H...O hydrogen bonds into a chain along the b axis.

Related literature

For related structures of sulfonamides, 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.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]).

[Scheme 1]

Experimental

Crystal data
  • C24H27BrN4O4S2

  • Mr = 579.53

  • Monoclinic, P 21 /n

  • a = 10.2583 (4) Å

  • b = 17.4727 (6) Å

  • c = 14.4375 (7) Å

  • [beta] = 97.199 (4)°

  • V = 2567.38 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.80 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.526, Tmax = 0.697

  • 19056 measured reflections

  • 5023 independent reflections

  • 3359 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.105

  • S = 1.02

  • 5023 reflections

  • 321 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 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
N1-H1...O25i 0.86 2.09 2.890 (4) 155
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 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: IS5200 ).


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]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
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]
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, o3061  [ doi:10.1107/S1600536812040792 ]

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.