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

Kumar, M.; Mallesha, L.; Sridhar, M.A.; Kapoor, K.; Gupta, V.K.; Kant, R.

doi:10.1107/S1600536812040792

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 (C-C) = 0.005 Å
R = 0.046
wR = 0.105
Data-to-parameter ratio = 15.6
Details

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

Mohan Kumar,^a L. Mallesha,^b M. A. Sridhar,^a ^* Kamini Kapoor,^c Vivek K. Gupta ^c and Rajni Kant ^c

^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-HO hydrogen bonds into a chain along the b axis.

Related literature

For related structures of sulfonamides, see: Rodrigues et al. (2011); Akkurt et al. (2011); Kant et al. (2012). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Duax & Norton (1975).

Experimental

Crystal data

C₂₄H₂₇BrN₄O₄S₂
M_r = 579.53
Monoclinic, P 2₁ /n
a = 10.2583 (4) Å
b = 17.4727 (6) Å
c = 14.4375 (7) Å
= 97.199 (4)°
V = 2567.38 (18) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.526, T_max = 0.697
19056 measured reflections
5023 independent reflections
3359 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.105
S = 1.02
5023 reflections
321 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O25ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

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.
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.
Kant, R., Gupta, V. K., Kapoor, K., Kumar, M., Mallesha, L. & Sridhar, M. A. (2012). Acta Cryst. E68, o2590-o2591.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2891.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds