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

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

doi:10.1107/S1600536812043668

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 (C-C) = 0.008 Å
Disorder in main residue
R = 0.042
wR = 0.103
Data-to-parameter ratio = 13.3
Details

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

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

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-HN hydrogen bonds occur for both A and B; the dimers are linked into [010] chains by C-HO 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); Laurence (2009). For related structures, see: Rodrigues et al. (2011); Akkurt et al. (2011); Kant et al. (2012); Kumar et al. (2012).

Experimental

Crystal data

C₂₂H₂₃BrN₄O₃S₂
M_r = 535.47
Triclinic, $[P \overline 1]$
a = 13.6081 (6) Å
b = 14.5662 (5) Å
c = 14.7502 (7) Å
= 74.439 (4)°
= 69.077 (4)°
= 62.581 (4)°
V = 2405.10 (18) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.920, T_max = 1.000
18681 measured reflections
8017 independent reflections
5364 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(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
_max = 0.34 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N8A-H8AN20Aⁱ	0.86	2.15	2.940 (4)	152
N8B-H8BN20Bⁱⁱ	0.78 (4)	2.28 (4)	2.974 (5)	149 (4)
C11A-H11AO1Aⁱⁱⁱ	0.93	2.47	3.372 (5)	164
C10B-H10BO2B^iv	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); 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: 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.
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.
Kumar, M., Mallesha, L., Sridhar, M. A., Kapoor, K., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o3061.
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.
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