N-(4-Amino­pyrimidin-5-yl)-4-methyl-N-(4-methyl­phenyl­sulfon­yl)benzene­sulfonamide

Taher, A.; Smith, V.J.

doi:10.1107/S1600536812046442

Volume 68
Part 12
Page o3362
December 2012

Received 15 October 2012
Accepted 9 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 103 K
Mean (C-C) = 0.004 Å
R = 0.046
wR = 0.116
Data-to-parameter ratio = 17.6
Details

N-(4-Aminopyrimidin-5-yl)-4-methyl-N-(4-methylphenylsulfonyl)benzenesulfonamide

Abu Taher ^a ^* and Vincent J Smith ^a

^aDepartment of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland 7602, South Africa
Correspondence e-mail: abut@sun.ac.za

In the title compound, C₁₈H₁₈N₄O₄S₂, the mean planes passing through the tosyl benzene rings form dihedral angles of 48.42 (9) and 15.1 (1)° with the aminopyrimidine ring. In the crystal, molecules associate via N-HN and N-HO hydrogen bonds, forming extended hydrogen-bonded sheets that lie parallel to the bc plane. The N-HN hydrogen bonds propagate along the b-axis direction, while the N-HO hydrogen bonds propagate along the c-axis direction.

Related literature

For the synthesis of related sulfonamides, see: Schetty (1969); Taher & Smith (2012). For applications of ring-closing metathesis (RCM) on sulfonamide-protected allyl-containing substrates, see: Yadav et al. (2011); Panayides et al. (2007a,b).

Experimental

Crystal data

C₁₈H₁₈N₄O₄S₂
M_r = 418.48
Monoclinic, C 2/c
a = 36.559 (9) Å
b = 6.9044 (18) Å
c = 15.524 (4) Å
= 103.852 (3)°
V = 3804.6 (17) Å³
Z = 8
Mo K radiation
= 0.31 mm^-1
T = 103 K
0.13 × 0.13 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.962, T_max = 0.969
11288 measured reflections
4459 independent reflections
3156 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.116
S = 1.04
4459 reflections
254 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.58 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO1ⁱ	0.88	2.16	3.036 (3)	178
N3-H3BN1ⁱⁱ	0.88	2.30	2.986 (3)	135
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5262 ).

Acknowledgements

AT thanks the National Research Foundation (NRF), Pretoria, for providing an Innovation Fellowship and Professor W. A. L. van Otterlo for his research oversight. Stellenbosch University's Science Faculty is also acknowledged for providing the laboratory space and addition financial research support.

References

Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth. Des. 3, 3-8.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Panayides, J.-L., Pathak, R., de Koning, C. B. & van Otterlo, W. A. L. (2007a). Eur. J. Org. Chem. pp. 4953-4961.
Panayides, J.-L., Pathak, R., Panagiotopoulos, H., Davids, H., Fernandes, M. A., de Koning, C. B. & van Otterlo, W. A. L. (2007b). Tetrahedron, 63, 4737-4747.
Schetty, G. (1969). Helv. Chim. Acta, 52, 1796-1802.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Taher, A. & Smith, V. J. (2012). Acta Cryst. E68, o1136.
Yadav, D. B., Morgans, G. L., Aderibigbe, B. A., Madeley, L. G., Fernandes, M. A., Michael, J. P., de Koning, C. B. & van Otterlo, W. A. L. (2011). Tetrahedron, 67, 2991-2997.

organic compounds