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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 [sigma](C-C) = 0.004 Å
R = 0.046
wR = 0.116
Data-to-parameter ratio = 17.6
Details
Open access

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

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-H...N and N-H...O hydrogen bonds, forming extended hydrogen-bonded sheets that lie parallel to the bc plane. The N-H...N hydrogen bonds propagate along the b-axis direction, while the N-H...O hydrogen bonds propagate along the c-axis direction.

Related literature

For the synthesis of related sulfonamides, see: Schetty (1969[Schetty, G. (1969). Helv. Chim. Acta, 52, 1796-1802.]); Taher & Smith (2012[Taher, A. & Smith, V. J. (2012). Acta Cryst. E68, o1136.]). For applications of ring-closing metathesis (RCM) on sulfonamide-protected allyl-containing substrates, see: Yadav et al. (2011[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.]); Panayides et al. (2007a[Panayides, J.-L., Pathak, R., de Koning, C. B. & van Otterlo, W. A. L. (2007a). Eur. J. Org. Chem. pp. 4953-4961.],b[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.]).

[Scheme 1]

Experimental

Crystal data
  • C18H18N4O4S2

  • Mr = 418.48

  • Monoclinic, C 2/c

  • a = 36.559 (9) Å

  • b = 6.9044 (18) Å

  • c = 15.524 (4) Å

  • [beta] = 103.852 (3)°

  • V = 3804.6 (17) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.969

  • 11288 measured reflections

  • 4459 independent reflections

  • 3156 reflections with I > 2[sigma](I)

  • Rint = 0.041

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

  • wR(F2) = 0.116

  • S = 1.04

  • 4459 reflections

  • 254 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.58 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O1i 0.88 2.16 3.036 (3) 178
N3-H3B...N1ii 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]; Atwood & Barbour, 2003[Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth. Des. 3, 3-8.]); 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.  [CrossRef] [ChemPort]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
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.  [CrossRef]
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.  [ISI] [CSD] [CrossRef] [ChemPort]
Schetty, G. (1969). Helv. Chim. Acta, 52, 1796-1802.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Taher, A. & Smith, V. J. (2012). Acta Cryst. E68, o1136.  [CSD] [CrossRef] [details]
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.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3362  [ doi:10.1107/S1600536812046442 ]

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